I just woke up and I'm taking my second sip of coffee as I type this. Thank you so much for starting off my day reading a GREAT post! That advice is succinct and ABSOLUTELY correct.
I've had two different bikes for a lot of my riding years and I can tell you it's a lot of fun having the choice of which one to ride each time you want to go out. Plus, when one of your bikes has to go to the doctor(in the shop), you still have another one to ride.
And YES, riding is more fun than working on them...for me anyway. I know that there are many here that get a lot of personal satisfaction from wrenching on them, and I am glad they do. If that's a part of bike ownership that makes them happy, I think that's great. It just isn't part that trips my switch.

 

I have a 2010 RK that I put a ton into like you did. Built motor and custom everything. I don't plan on getting rid of it but I ride the crap out of it and my 2017 SG. fIt's as reliable as anything else I have. IMO honestly your issues don't sound that bad. Stators and regulators are know issues and so is the starter. The belt.... Well she is 130/120 now so that is really not what Harley was counting on the belt to withstand. I have had at least two bikes in the garage for decades. I can work on one while I am riding the other if I have issues.

I agree with what the others have said in getting to be able to do the work yourself and find a good indy (which it sounds like you do) for the stuff you can't handle.

 

I'll be blunt: unload the '03 RK and move on.
IMHO, you'd be extremely lucky to get $4K-$5K for it, in its present unreliable condition, so don't be stunned when you get offered a lot less, if you get any offers at all.
There are plenty of '03 - '08 RKs being sold at a good price with a fraction of the mileage.
If you find that you miss your RK, then buy another low mileage one.
Then you can start doing your own standard maintenance (change oil, air filter, lube, etc.) on your next RK.

 

I agree with ya here. What *might* or actually likely happen is, I'll just add another bike and keep the 2003. Regardless, I won't be adding or selling a bike for probably 1-2 years due to saving for a home.

I think you're right about my issues not being that bad. I think most of it's in my head. Seriously, being stranded 3 times with in 3 weeks does a number on you when you're a long way from home. The belt actually probably snapped from getting a rock caught in it. I had just gotten done navigating a gravel section of road will in the middle of Missouri. I had no idea it was going from tar to gravel. Had about 10 miles on it. About 10 miles after I got off of the road, it snapped. Plus, the belt had been replaced during the build less than 10K before it.

Anyway, you're right. The bike has been pretty reliable for the years/mileage and outside of 2014-2015. This is the first issue to come up since then and 8,000 miles or so.