here are my worthless ramblings:
1. No to both - unless you are looking for an excuse to not ride anymore, then yes.
2. No, I finally bought my LT after a couple years of indecisiveness, 1 month later (almost to the day) I got an infant and so I have even more years before he can ride with me than you, but I know that if I exercise it from time to time and maintain it that it will still be running great when I can finally start to use it for its intended purpose.
3, 4, & 5. Yes, if you are concerned about it, I would suggest that you change the fluid in the final drive and transmission at the same time. The final drive is super easy, easier than an oil change, the transmission is a little tougher. Make sure you inspect the drain plug magnet and look for evidence of a problem (take picture if you are unsure of condition and post as a question to this forum for expert opinion). My limited understanding is that the two places that you can get contamination on the clutch are from the clutch hydraulics or from the transmission fluid, someone will correct me if I am wrong. Measure the amount of fluid you take out of the tranny vs. how much you put in and see if there is a significant difference. Watch your sight glass on the clutch cylinder and keep an eye for any loss of fluid there. If neither of these proves an issue, then unless you or a previous owner abused the clutch you should be fine, and if that is the case you shouldn't sell it to some unsuspecting schmuck like me with a known bum clutch.
6. Not just no, but H-E-double-hockey sticks no, unless you just have more money than you want to keep. Service is not hard as stated above, just time consuming.
7 & 8. Nope, ride the bike and enjoy yourself.
10. As far as I know, if you use the clutch properly as described in previous threads stop and go is not a problem. After all, the clutch was designed to be used for hundreds of thousands of miles of various driving conditions.
11 & 12. Don't worry about the grime being there in the first place, if you haven't been cleaning it regularly it tends to build up, you drive on roads where other cars leak oils and stuff, which gets picked up and sprayed on your bike over the miles. I do prefer to keep a clean bike but at the moment mine are both just plain disgustingly filthy so I can't really preach here.
In short if you are looking for an excuse to not have a bike anymore, all of these are good excuses. Personally I can't imagine giving up my bike for a mass-transit ride but that is me. I know there is increased risk just from being on the road, but I also think there is a concurrent reduction because I keep my skills practiced and in common use. I see these weekend Harley riders and watch them and I am amazed that I don't see more accidents on the weekends. All in all make your decision based on what you want to do and ignore all these possible problems, after all it sounds like you could do the work yourself and it just might take a few months, you'll find it rewarding and save a bunch of money, and then you know that part is proper and fit.