I'll add some second-hand (or first-hand, or maybe like 1.5-hand...?) perspective on both the Honda 250's that may give you some peace of mind. I ended up finishing my own TAT run in 2015 with a British rider on a standard 250L who had virtually no offroad experience before shipping the bike to the States and riding the whole route including GPS Kevin's NY-to-TN extension. (I was on an XR650R and will wholeheartedly commend any choice you make that has electric start. I think I still have tendinitis in my kicker leg.) I also ended up hosting another Brit at the end of his run before he flew home and he used the Rally. In his case he actually bought the thing sight-unseen from a dealership in Florida, farkled the it there and at various hotel parking lots for the first week or so, and then just got on with it and plowed on through to OR. He too had extremely limited offroad experience, though he had some years of on-road under his belt. He posted some of his own thought process here and then went into a different RR thread afterward that you might find applies pretty well to you. Long story short, they both made it, they both did fine, and they both had a blast. Capability difference between the bikes can really just be measured in a few percentage points. Concerns about bodywork damage on the Rally proved to be mostly unfounded - he spent a few hours cleaning and polishing at my place after the trip and it barely looks like it's done a few trail rides, let alone 6k-ish miles coast to coast. The only mechanical issues I saw between them were leaking fork seals (get Seal Savers and be done with it) and the 250L needed new clutch plates after arriving. But I later found out that he bought the bike used from a guy who had already done the TAT on it before him... and then continued down to Venezuela. After a new clutch and new fluids everywhere, he picked the bike up again last year and spent 5 months riding down to Buenos Aires with no issues. Reliability and durability is really no concern with these things. The biggest complaint I heard from both was power, or lack of it. I heard it most about the Rally but that was completely stock mechanically. The 250L had an exhaust, but by the end of the trip he actually wanted the stock exhaust back on because the droning was so sharp and irritating on longer stretches. We put the dB killer in the muffler before he left for South America and it hardly did anything to help. Ultimately it seems if you want more power out of a 250 without mucking with stock reliability, you just buy a bigger bike. On the flip side, they were both far more maneuverable than mine was in the technical sections and had much sturdier rack selections. If you're already active on here and seeking advice, that to me means you already have the mindset to pull this off even if your on-bike experience is limited. You're not biting off more than you can chew because you've already started chewing. I also had embarrassingly low hours on the dirt before my trip, and I still made it on an oversized ex-desert race bike that was kickstart-only and refused to acknowledge the existence of even that if the engine was any warmer than a freshly peed-in wetsuit. I can say though that the eastern half serves as excellent training for the western half for a lot of reasons: it gets you used to different types terrain individually before you have to deal with them all at the same time out west, it gets you used to being on the road for weeks at a time, it gives you time to acclimatize to the bike, you get to practice picking up after tipovers in fairly even terrain, you get to practice rerouting on fairly benign routes before trying to find your way through the spaghetti clusterfuck of Oregon logging roads, and on and on. But as someone else has pointed out, you're still doing this in a first-world country. If you're anything like me, the stress of thinking about all of it and trying to perfect your setup is way higher than just doing it, and far less enjoyable. Keep in mind you're doing this for the trip and not for the bike. The bike is just the tool and they're all so good at this point we're just talking about different flavors of vanilla. My guess is you're already pretty well informed by now, so go with what settles best in your gut, get it in your garage, and then spend more time on the bike building confidence than listening to a bunch of monkeys like us converting molehills into monster truck ramps.