Hi Scotty.
I ride an 88 cube '03 Dyna Superglide, had it 4 years and I know the previous owner who had it for about the same time. She's done 33,000kms with no major work or issues that I know of..... yet. She runs fine and has no oil leaks to speak of. It just gets regular services at about the right kms irrespective of the time. Yeah, it struggles at times along side the newer models with the bigger cubes & upgrade kits but it does everything I ask of it. Get something with relatively low kms for the age and something that's obviously been cared for. You'll know when you see it. Don't hold back!
Welcome Scott Morris-on a Harley Davidson.