Sold my 99 Electra Glide and now am looking at a 2002 Softail Standard. Previous owner has done the following:
Thunder header exhaust
Hypercharger
Windshield
Quick detach backrest
Solid leather bags
Bike has about 31k on it and they want 6k. Bike also has about 1.5 years on the transferrable warranty.
Now for the big question/concern. Don't expect the 88 will give me the performance I want. I want more power plain and simple my V-rod spoiled me for that (Sold it). What are my options and the associated cost? I want something dependable so nothing radical here. Or are there other options such as buying a high mileage later model for less and building that one up. Not firm on a Softail just that's what I found first. I've had a Dyna, Electra Glide and V-Rod all had pluses and minuses. Love the power of the V-rod, Comfort/bags of the Electra Glide and The Dyna well was my 1st Harley so it was special although the 96 with the 6 speed was nice.

 

It looks like you had a diverse family of bikes in your history and also seems like you want to wrap all of those into the bike that you're looking at, and it's not possible. If I were you I would look for a 2010 Softail and apply all of that money that you would have put into the 2002 with all of the modifications to bring it up to your expected level of performance and be done with it. Your modifications will run you around $3000, so add that to the $6000 on the bike that you're looking at, and put yourself into the 10K price range. you'll be happier and have a more reliable bike, with a better warranty.

 

Yeah unfortunately I get bored quickly with what I'm riding and want something different. My only rule is it has to be a Harley. Problem is if I buy to new I will loose my shirt when I trade. So far I have been lucky and have broken even every time but my luck will run out eventually. I just hope it doesn't until I've found the perfect bike for me.