[husker boxster]

There are many on the forum that use their Boxsters year round, including in winter conditions. My daily driver rotates between my Boxster and Cayman. I use my Cayman in the winter but I put Blizzaks on it. Gets around fine on ice and snow < 4". A 986 will be the same as long as you use dedicated snows in the winter. Never drive with summer tires on wintery conditioned roads (it will only be a matter of when you crash, not if) and don't waste your time with all-seasons since you're in CO. Get a set of snow tires and dedicated wheels for them and you'll be fine.

Boxsters are very easy to work on and routine maintenance is possible for the DIYer. There are plenty of articles on how to do many maintenance items. And with a few unique tools in your tool box, you'll be ready to tackle most jobs (star and hex socket sets chief among them).

It will be hard to compare what someone paid for their car because of when they bought it, how many miles it had, and what condition it's in compared to the one you're looking at. I would suggest looking at multiple Craigslist ads from numerous cities to get an idea what mkt value is, keeping in mind that supply and demand influences price. So prices in LA will be lower than in Kansas City. But they will give you a feel for the mkt. You can also look at some of the price guides like KBB or NADA. I like to use NADA and use the following formula when calculating a private party price - go half way between clean trade-in and full retail. AutoTrader and PCA.org are also places to look for pricing, but they'll be a bit higher.

Your estimates on IMS failure appear to be in the ballpark. Let's not turn this thread into another IMS debate. It sounds like you've done some homework, but if you have several days to kill, search on IMS and read everything you'll ever want to know. That horse has been beaten to a pulp many, many times before in tons of previous threads.