"Clutch slips leaving me on the side of the road on 3 separate occasions, even after a full clutch replacement and cable adjustment."
On this check your clutch, sounds like something is off there. Do you have enough play in clutch lever? Some think a dime width of play at the hinge is good.

"Now, on top of all that the bike engine dies when handlebars are turned straight to ride off and won't start again until returned to resting position."
Cables/wires are binding somewhere from the sound of it. If you turn the bar straight and it dies, then something must be getting bound up or pulled too far? All wires and cables should have slack through out the range of the handlebar's movement.

 

I actually have a 99 Sporty that has been built, it only had 6500 miles on it and didn't run when I got it, just as you,had to put few bucks in it, but I went the performance route not stock, and run run it does. Good Luck sounds like you got a 20 year old bike that someone abused and now you know what you will have when YOU are done with it as I.

 

sportsters are generally reliable + their engine design is superior, but any neglected bike can be a costly nightmare!! once read where HD wouldn't copy the sportster engine design for the "big twins" because it was too costly!!!! sorry just what i read + yes i am a sportster fan!!

 

sorry to see you have issues but even when hd was crapola, their machines were only as good as the people who bought them. my 1974 ch still going at 175k miles with basic maintenance till recent when i tore down for frame paint and decided to up the ponies. this was at 150k miles and the wear was nill and jug taper around .006 and a .010 cleaned it up. the original pin wear was really not measurable since i did not have the original setup, anyway i replaced it with s&s wheels for the remake.
my 2001 sport still humming and i flog the crapola out of it, built as a high speed machine and i take it t 7.5k rpm many times and will peg out the speedo when i drop out of third.
so it is what it is.

 

Alright you have a blank canvas...
Build upon it, make it your own.
883? No more bore to 1200. And play with it from there.

 

A 19 year old motorcycle needs replacement parts? We'll keep a look out for it. Thanks for the "heads up."

 

Let me give you a piece of advice you wont like. Put that bike on a charger or buy a new battery and put it on craigslist. Let some other poor sucker deal with it.
For what you'll have into it, you could easily buy a newer Dyna or sportster if that's what you want.

 

Good Luck to you.... get yourself the factory service manual and have at it. Sounds like some minor stuff to tend to, which will help you become familiar with it.
There is another forum specific to Sportsters.... XL Forum ..... I have spent a great deal of time there. Like this joint, it does offer lots of good info, lots of ragging/tagging, some will bust your chops, others will give you the shirt off their back. In all it is an excellent forum for Sporty's... just as this is an excellent forum for HD owners!!!

 

you are probably right and I have definitely been considering

 

this is more than just "replacement parts" this is 3000$ in torn up ****, not just average wear