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Buy what you will be happy with.
I bought my 88 1500 early this year, I have not regreted it a bit! I love this 88 !
It had a broke idler gear for the starter drive, an engine out job to fix, I knew that when I bought it and been happy just roll starting all summer and fall so far.
I'll fix that gear soon this winter if I ever stop riding it long enough LOL
The only other thing was the throttle cable broke, cost me about $10
I put on new tires, the old ones were good but I planned a ton of miles, many which I did not ride, so the tires on it would have lasted the season I think. I wanted good spares on hand anyway in case I ruin a tire so changing them early was good for me anyway.
Buy what you want with the options you want that you can afford.
I was ever so lucky to get my 1500 when I did at a price I could afford! I don't mind a roll start, or the work to fix it soon, reverse works great, no other real problems for me with it
I have never financed a vehicle in my life, only pay cash, and this 88 1500 is the first thing I ever carried more than just liability on, full coverage on this one! I know if it got totaled I would never find another I could afford!
So far I'm not sure what the talk is of 4th gear problems, this 88 has been fine but I only put about 8k on it maybe this year, it has about 178K now. Something like that, I don't really watch it that close, I thought it was 180K but noticed the other day it was a bit less.