School me on full size trucks...

Yes, the turbos.

I'm going to expand on the trailer comparison. I'm using Haulmark, as an example, as they have a wide variety and are steel-based like what most people buy.

5'X8'X5'6" is 935lbs wiwth a GVWR of 2980lbs.
6'X12'X6' is 1325lbs with a GVWR of 2980lbs.
7'X14'X6' tandem is 2125lbs with a GVWR of 7000lbs.

As you can see, the tandem is more than double the weight of the 5'X8'. This is not only because of the additional axle, it'll have brakes on at least one of those axles, heavier frame, heavier floor construction, and heavier ramp door (if equipped). This is so it can handle the heavier loads it's designed to carry. The additional axle means extra rolling resistance of two more tires and tire scrub when turning. The longer trailers are, usually, taller, which means more wind resistance. All this, combined, is why a tandem pulls harder.

Here's what I've experienced in leaf-spring versus torsion-spring axle. A leaf-spring axle rides far more harsh. I have a 5'X8', leaf-sprung lawn trailer that rides far more harsh and noticeable than my 7'X12' torsion-sprung box trailer, which is three times heavier. In a shorter 14' tandem, like you're considering, a leaf-sprung trailer will exert a lot more tongue weight. With a torsion-sprung trailer of that length, the axles carry their weight individually. The front axle will, generally, support the front of the trailer with the tongue jack fully raised. The US Cargo tandem I used to pull could be moved by one person. I could push down on the tongue and pivot the trailer on the front axle, to maneuver it into place. With a leaf-sprung tandem, the axles share the load, as they're connected by a rocker between the two leaf springs and the weight "pivots" on that rocker (think of a see-saw). Therefore, it'll exert a lot more tongue weight. The torsion-sprung trailer will pull much nicer and put much less load on the tow vehicle. However, because they don't exert a lot of tongue weight, they will cause a 2WD truck to get stuck much easier. I've been stuck in someone's backyard, on wet grass. We had a 5'X8' leaf-sprung, 7'X14' torsion-sprung, and 8.5'X24' leaf-sprung. I always took the torsion trailer, because it pulled so much nicer.

Many inmates are posting what their trucks have towed. That's fine. But, when you pull a trailer, everyday, as part of your living, that's a totally different scenario. There are many forums (like here) on people who tow for a living. You won't find many doing it with a gas, 1/2T truck. For longevity and profitability, it's difficult to beat what a HD diesel pickup offers. As mentioned, the older, non-EGR/emission diesels are the way to go, as they're less complex, more reliable, and more fuel efficient. I suggested a 4X4, because the Dodge and Ford are solid front axle, which means better tire wear, when being used as a tow vehicle, and less chance of getting stuck (annually, one tow bill will be more than the extra fuel useage of a 4WD). Lastly, if you're not doing your own routine maintenance, learn how. A diesel means more oil, a little more expensive filter, and a regular changing of the fuel filter (thanks to ULSD fuel). But, as mentioned, the intervals will be further apart and you're not killing the truck while using it.

Avoid the Ford 250s with the 6.0 diesel like a plague. They are know for head problems, and it is not a cheap fix.

If you are thinking about a Ford diesel, here is a good link.

http://powerstrokehelp.com/7.3liter/7-3_main.asp

I have the 5.4 in mine. It is a 2004, and when I bought it the 7.3 was no longer available so I went with the gas instead.

Has 140 thousand on it, and only thing I have done on it is routine maintenance, 2 fuel pumps, an alternator, and ball joints. Other than that it is still running great.

For sure, a POS!!!!!

We had one 5.4L. The only thing we did was routine maintenance and had to replace the timing cover gaskets. The two 6.8L only needed routine maintenance. The 5.4L only got 1-2mpg better mileage and was definitely working harder.

Ball joints are a given, on the Superduty. But, they're not hard to change.

With your budget I would rule out diesels as they will have a million miles and run into the ground. My dads had a few f250 with the5.4 and its no power house but will get the job done.

I had a lb7 duramax with 200 k that was reasonably easy on the wallet. I sold it because the injectors worried me and the repair bill is huge. I probably got 18 mpg running a tune and being easy on it. Sold it to buy an fj cruiser which I liked but it got the same mpg and lost the bed etc

I wanted another truck and thought about a newer diesel but just didn't make sense with the difference in fuel prices. Around here it's an $0.80 spread. My 07 tundra gets 15.6 mpg so it's cheaper to run.

I've had my tundra for a few weeks now and it's sweet. it hauls ass very comfy and the buy in was much cheaper than a comparable diesel. Mine is the co crew cab limited with leather navigation etc.

I don't haul trailers alot so I can't comment on towing mileage. I did look at the titan briefly but didn't like the interior and I drive a lot so it was important to me. I think the tundra looks nice too.

I have an '08 4wd Titan. The axle issues were fixed in 08. I only have 65k on mine, but it's a good truck & hasnt given me any trouble. The drivetrain is solid. I liked that you can get the crew cab with a longer bed than 6 1/2' (mine is 7'3") and I can close the tailgate with 2 bikes in the bed. I have a few complaints though. The paint is not very durable...it scratches easy. There is too much plastic on the truck & the cowel in front of the windshield discolors quickly. Also the OEM brake rotors warp easily.

if you are committed to yanking a trailer a large % of your driving time. hands down go with diesel!

mid-size gas trucks suck at mileage when towing any kind of loads. extra wear and tear on a gasoline motor exceeds diesels by a mile. mileage for a 12v Cummins is 20-24 mpg... yanking a trailer loaded with 15k+ lb, 16 mpg.

pretty bias but IMHO the absolute best small truck on the road is 12v Cummins Dodge made 1994-98.5. with 1996 being the most trouble free. ask any long time Dodge dealership mechanic and they will tell you... once they sent out 96 12v Cummins... they never saw it again.

main drawback to 12v Cummins is... a low mileage mint condition 12v are like hens teeth to find. then expect to pay same as a much newer Cummins truck.

took me almost 3 years to find my 96 12v Cummins, 4x4 2500 extend cab, 5sp with 67k miles in like new condition. paid out the nose for it... best truck I've ever driven.

that was 5 years ago, now at 110k miles... besides filters, the only thing done was a full ceramic clutch I installed about 35k miles back. reason that was done was to make sure clutch could handle the very lightly modded 400hp output.

besides new full ceramic clutch ($355 Oriellys), next to zero maintenance costs for last 50k miles with my 12v Cummins.

o0pss... forgot to add $500 for factory takeoff wheelset with zero miles from a 2012 2500 Cummins truck found on Craigslist.

Good luck finding a 6.4 diesel or an Ecoboost for $15~20k that is in good shape.
don't forget, the OP has a budget.

The budget isn't that big of an issue. My stepdad owns a car lot and runs across ridiculous deals all the time. Passed up a cherry '08 Silverado LTZ for $8800 this summer because at that time I was hell bent on ditching the trailer and getting a Sprinter.

I had an 04 Titan that was a good truck but IMO it sucked balls for towing with. It liked to shift way too much and got terrible mileage. It looked cool though

Previously I had a 7.3 excursion which was essentially trouble free up to 175k miles, but finding good condition 7.3's would be tough, plus those things are getting old so you are going to see a lot more stuff dry out/leak, etc now a days.

A couple years ago I had an 05 Duramax crew cab and that thing was great. If you go Duramax you want 04.5 and later to get the more reliable injectors. I got nearly 20 unloaded and 9-12 with a 24' enclosed.

The thing with diesels is that towing is so much more relaxed-you can go up a pretty steep hill at 70 and it won't even downshift. The brakes are better, better transmission, suspension, etc. The maintenance isn't really that bad especially if you are doing it yourself. Also you have to look at resale-yeah they are more to buy, but you can sell them way easier and hold their value well. Once you've had a diesel, its very hard to go back.

I would think you could find an 04.5+ duramax fairly easily in your price range. I think I got 21k for mine 2 years ago with 100k miles, crew cab, leather, etc. Hardest thing is finding one.

if you are not interested in the best, which are 12v Cummins. the next best are 7.3 Ford 2000-2003 seems to command highest prices.

super tough motors with a late model body

With the amount of miles that the OP puts on annually, a diesel makes lots of sense.

We recently traded our '07 Chevy 3/4 ton x-cab gas (becoming a rust bucket) in for a '12 Chevy 3/4 ton crewcab gas to haul our truck camper. Nice truck and the 6 speed auto is MUCH better than the older 4 speed.
Because of riding the bikes, I cut way back on driving it to the office during warmer weather. Maybe 10,000 miles/year, so going with gas makes $$$ sense for me- the truck gets around 10-11 mpg.

But upwards of 30,000+ miles per year plus towing? The $$ premium for an oil burner is a no brainer. Better towing, much better fuel mileage.

Those big dodges you may as well just take them in and have the subframe braced. They crack, often.

Feedback from a friend who is a Nissan product development engineer: Do not buy a Titan.

I manage a fleet of vehicles that includes Tundras from 2000 on, GM's and Fords.

Tundras are ok as a weekend warrior truck. The only good I can say is the engine is strong. As mentioned earlier the body is made of cheap, thin metal. The wheel wells bend under my feet (165#), the bumper can be flexed downward with the push of a single finger.

My 2008 (160000 miles) double cab long bed can barley make it 300 miles on a tank of fuel which means a refuel everyday. By comparison the 2500HD I drove prior to the Tundra got the same 12 -13 mpg and could go almost 400 miles on its appropriately size fuel tank. After 13 years in production Toyota still can't put brakes under it that don't warp rotors within a few thousand miles of use. We see 40000 miles plus out the Chevy and Ford brakes with few warped rotors.

Toyota's goofy looking exaggerated long wheel base makes it very difficult to maneuver in tight areas. Everything about the Tundra feels and looks big just to be big.

One last thing, crawl under the Tundra and look at the cross members, or lack of, in the C channel frame.

If you are buying a truck to work with stick to Chevy, Ford and maybe Dodge.

OP; any developments?

I'm in the same boat as you with the same budget, interested to hear your thoughts, as I haven't found a solution I'm happy with yet.

Seems there's a plethora of 5.3L cat-eye body style silverados with around 100k available for ~$13k. It's actually pretty tempting to try and save a few grand for a higher mileage truck that gets decent fuel mileage with a motor known to do an easy 200k, even though the interiors are gawd awful.

Diesels around here in my (our) pricerange mostly have +170k miles, except for the 6.0s which I want no part of.

I have the Chevy like you said and its a nice truck but if you are pulling a trailer a lot then get a 3/4 ton withe the 6.0 because you,all really work the 5.3. Most 1/2tons could work but limit you if you want a bigger trailer later on.

Like you said with diesels, any decent priced ones will have tons of miles and then require work that adds up fast.

Without Hijacking any further; I'll only be pulling a small boat and a snowmobile trailer with a few sleds, so a 1/2 ton should be fine for me.