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The deal breaker would be paying $6,000 for a '98.

 

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Mileage, 88 ci's aren't good unless you change the cam boots regularly. 96 ci are good. 103's good but cost more. 96 ci 6-8 k depending on miles. Just get an fxr and buod motor if you are a mechanic, if not 96 is best option, same stroke as 103, can always build into a 106. Plus the 96 has a 6 speed. Shovelheads are nice too, but not as fast as an Evo. Requires more maintenance, has rigid mount, but nothing like a kick start bike in the world. Not even the new bikes. Which are nice but not comparable to rebuild able real Harley's.

 

I'm always cautious of engine upgrades without mechanics receipts for the labor. I am meticulous in my garage, but I've seen far too many "shade tree mechanics" who aren't. Bolt-ons are pretty safe, as they're mostly dummy proof, but internals are another story entirely.

Also, ANY item to indicate the bike may have been raced or ridden overly hard. Sometimes this is a piece of equipment or a marking on the bike, sometimes it's the seller himself (I generally don't buy from kids who proclaim how "fast" the bike is).

Beyond that - uneven wear (tires, belt), signs of significant leak (gummy build-up on the undercarriage)...

YMMV.

 

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Yes, ...... on the paintwork would be a deal breaker for me.

 

Each engine has had different strengths and weak points. I don't think any are "bad" I have had an Evo (80 ci) and 88 ci (twin cam) and a 96 ci (twin cam).

I have really liked them all and rode the tar out em. The evo was great, single cam. I cammed it up and it ran great. Replace the cam bearings when you do so with better ones. The base gaskets weaped a little (I didn't care). The 88 twin cam is a beefer motor I cammed it up and replaced the cam tensioners with the hydraulic set and it runs great. I also replaced the main bearing when the race pushed out and caused a leak in the primary (between the trannie and primary). I love the 96 as well but it has some issues that will need to be addressed.

Nothing wrong with any of them. All engines have some weak points just address them when you can and the thing will run forever.