HarleyTechTalk

The ignition switch can be disassembled (carefully on a tray so as not to lose small pieces) and cleaned. It is pretty simple.
Is it still a vacuum operated petcock? Is so, does it have a new vacuum line? Have all vacuum lines been inspected/replaced? Personally I am a fan of mechanical petcocks like Pingel.
Next time it dies, try starting with some carb cleaner or starting fluid sprayed directly into the carb. That should point to fuel or ignition.

Why wouldn't you?

Quote from: ziggy24 on Today at 05:01:10 AM$12,000.00 Yikes!

Almost free

$12,000.00 Yikes!

Hello, recently built my 14 limited 103 into a 107, bike runs great but I had to repair a cylinder base leak o ring. My question is with only 1800 miles since my build, I m thinking of putting the engine back together using the same piston rings? Thanks for all comments.

Appears heat is likely not your culprit either. I think you've reached the "get down on your knees and pray" - I mean, closely inspect the various wiring points where these culprits tend to hang-out. Recommend a good HD service manual for the wiring schematics -  likely can source the schematics on-line for an older ride by now. Where you have a 26 yr old, don't overlook cleaning the Grounding points for corrosion.

Calf Phil noted the ignition switch up on your tank. That's yet another source of gremlins many folks have experienced. As well Hogmike, Speedy and fbn ent have provided possibilities you can verify.

An added benefit to all your efforts is the "getting acquainted" aspect of your new ride when going this route. You'll thank us later.

Short of that, where the issue is so intermittent, you just may be up against the expensive route - the Ignition (Compufire or other quality item) entirely driven by blind parts replacement followed by coil(s), followed by, (Yes, coils can be tested first) Ignition Switch, followed by.....

Any issue with contacting the previous owner to determine history? Be nice and he might open-up. 

Try going for a ride with the cover off. If it's heat related it may help solve it. I had a Crane HI4 go bad but spent months chasing fuel gremlins because I just knew it was running out of gas. And now I run points. With points they either work or they don't

Thank you.

Quote from: Tacocaster on Yesterday at 06:35:12 PM70+ for 2 hours? Doubtful it's a gas cap venting issue but stranger things have happened.

My personal experience has shown the Compufire Ign. can and will fail but it won't kill "everything". So again, in the interest of clarification, when the engine dies do you still have lights and all running electrics alive?

Why? you might be asking. Because a mains failure will shut down an engine quickly but it also takes "everything" else down as well and self-recovery after a few minutes can be typical of some breakers when affected by heat.

A consideration to note, your Compufire may be expanding from engine heat and opening the trace on the printed circuit board when it expands (bends). I had a taillamp circuit board do that on my 07.

Wonder if the previous owner ever experienced this issue?

I haven't riden it at night and I didn't check to see if the lights were still working. The first time it died, the bike cranked over but wouldn't fire. This was on the ride home after I bought it. It was pouring rain and the wind was gusting 60mph. It died about 1 hour in and I thought it might be something electrical ha ing issues with all the water. My son was following in .y truck a d I had a can of fuel in the back so, just to make sure it wasn't out of fuel,  I put a little less than a gallon in.  I was afraid to keep the cap off a y longer because of the torrential rain. After 5 minutes or so, it fired up and ran perfectly for over a week. The 2nd time was dry and cool and it died about 40 minutes into the ride. I got stopped and checked the position of the peacock out of habit, then tried the starter and it fired back up and ran perfectly for the 40 minute ride back home.

I don't know if heat is an issue as the warmest temperature I have ridden in so far is the low 70s with most rides being in the 60s and even high 50s.
This electronic stuff stumps me.  I have no experience working with this type of ignition.
I bought this bike as a donor for an Evo chopper project. I never expected to like it as much as I do. I'm really hoping to get the bugs out by next week as I have 2 weeks off and I would like to take a trip on this thing instead of tearing it completely down like I originally intended.

Thanks for following-up and providing your findings!
Happy trails!