Welcome, Mike! I'm pretty new to V-Stroms so can only tell you that my first generation 650 (2010) is amazing. All of the 650s have potential problems with the stator/RR combination, so you should either be sure to buy one that has an upgraded RR and a voltmeter, or budget to make those changes immediately.
This is a very broad statement and does not really reflect reality. Other makes also have stator failures, so I would not use that as a decisive criteria. Yes install a V meter if it does not have one so you can monitor the health of the system.
Now to your questions. They have been asked before so spend a little time and do a google search on this site or including stromtrooper in the search string. You will find a lot of good information.
There are differences between the different models, not so much from year to year. So I would say don't worry about what year it is, that is not a decisive factor. You need to narrow the choice by how much you want to spend and what features are a must, like ABS which the oder models don't have.
Mileage: There is a 2002 VEE with over 400k miles so don't get scared by a bike with 40k or 60k at the right price, if it has not been abused.
There will be may older bikes that are perfectly fine, if you can live without ABS. They will be well farkeled and likely be a real bargain. They don't hold value well unlike a BMW or Harley, so you will get a lot of bike for a reasonable cost making it a low risk investment. If you really don't like it you can probably sell it again with little loss.
Look here and if need be do a fly and ride. You are likely to find an honest deal from members here. Plus check Craig's list and e-bay and try to buy in the off-season for better prices. Always find out why the bike is for sale. Many get bit by the new bike bug and then the old one needs to go. That's the one you want to buy.