If you're handy with a wrench, DIY. Changing the pads ONLY would be less than $200. Doing the hydraulic upgrade yourself with a cam upgrade and tools is about $900. Not terribly difficult.

 

If either of the bikes are offered through a HD dealer ask about extended warranty?
the evo probably not, My story Long story short I got stranded today via my 98 evo on the way to work electrical? lost a days pay plus tow bill and repair. lol. I'd suggest Twin cam I am just a tad discussed with my evo, If the softail custom was still offered in the HD line I would have bought or ordered one this afternoon, with the twin cam tensioners plan on the upgrade or changing those nylon tensioner pads out ASAP,
don't get me wrong I love my evo but? it is 17 years old and with out parts on the side of the road well you get the drift. Twin cam!

 

Sounds like a bad day for sure. All the bikes I am looking at are individually owned so it's take it like you did your wife for better or worst.

 

I located an 02 today with only 10,000 miles on it he is asking 8000 I have only saw pictures of it might be worth checking out.

 

quote above this was earlier today
there are some great buys and bikes out there, when I was at the HD dealer today fellow getting a regular service had a 95 evo softail there that was cleaner then most on showroom floor less then 25000 on odometer, you will know when the deal and bike is right if you are not 100 percent walk away still a buyers market
oh the worst part of my day was not breaking down the thing that was really unnerving a dozen or so bikes passed and not a single one stopped

 

American Iron Magazine has a good article on cam tensioners by editor Chris Maida. issue 313 on sale until 8/19/14. Cam tensioners wearout due to rpms not mileage. That us why city driving is harder on tensioners