I've never paid $1500 for a bike! I'm not even sure that any of mine ended up costing that much even after the rebuild... I love my cheapies.
My "first" bike was a free '86 Radian that I found on the curb on garbage day (!) Knocked on the door, asked the guy if he was really throwing away a motorcycle. He said yes, I pushed it home two blocks on two flat tires. I was 14 at the time and had little to no idea of how to fix a motorcycle, and when my mom found it in the shed, she made me get rid of it.
My first actual bike was a $400 '79 CX500, which I sadly no longer have. I tried to turn it into a cafe racer but, being 17 at the time, didn't really have the skillset I do now, and it just ended up being an ugly lump. Reliable as hell, though.
Next was a $400 '78 GL1000. This one was actually two bikes I bought as a lot - one with a bent frame but running motor, and one with a usable frame but seized motor. I spent about a year and a half doing a frame up restoration/reassembly on this one. By far my favorite bike out of all I've ridden. No, it doesn't go as fast or turn as hard as a modern bike, but something about it "feels right." I still have it, recently rode it for a 3-day tour of the Upper Peninsula:
I also recently acquired a "free" '93 GL1500. It's a basketcase, which is why "free" is in quotation marks. It's mostly there, but damn the plastics for these things are expensive. It'll probably end up costing me about a grand to get it on the road:
And finally, I bought an '83 CX650 last weekend for $500. I just started a build thread on this site.
I do have the tank and body panels, but the bike actually looks better without them!