Advice for a potential Mini buyer - The MINI Owners Lounge

Seriously considering becoming a Mini Owner in the near future...but need either a little more convincing or some one to talk me out of what might be a decision based on emotion rather than practicality. I guess I’m looking for arguments either way (though to be honest, I hope the convincing arguments are more compelling, because I really like the cars!)

Anyways, the primary purpose will be for commuting, about 70 miles daily R/T, often in heavy traffic. Currently racking up miles (and a fair amount of gas) on a 2002 Honda CRV for this purpose, which we would like to keep for a while for its size and utility. Like all Hondas, its been a reliable car, even with my abuse, and about the only thing I’ve had to replace was the clutch at about 80K miles a month or so ago. Our other car is a 9 year old Infinity G20 with about 112,000 miles that still runs great and I’d like to pass on to our 17 year old daughter. So I am in the market for a good economical car, and with as much time as I spend on the road, I’d like it to be something fun. The Mini seems to fit the bill, but I have a few questions that maybe someone can help me with.

1. New vs. Used. Generally don’t buy new cars, although I have leased a few. Because of the rapid depreciation that generally occurs in the first year or two, I’ve had good luck buying low mile, 2-3 year old cars to be a pretty good deal. I know Mini was redesigned in 2007, although pains were taken to keep outward appearances relatively unchanged. That said, are the new engines in the base Coopers significantly better in the 2007/08 models significantly better than the 06’s?
2. S vs. non-S. I know it’s a matter of power and to some that also translates into fun, which to a degree that might be true for me as well, but due to the kind of traffic I drive in I probably wouldn’t be able to reap the benefits a good deal of the time anyway. Also, am I wrong in thinking that the supercharger in the older models or the turbo in the newer models are just one more thing to go wrong? Or is this risk negligible?
3. Reliability. This one’s a little scary for me, as on this board and others, it seems to be a main topic of discussion with respect to Minis. Is it as bad as some might make it sound? I’m ok with stuff needing repair once in a while, but really don’t like to be a regular at the repair shop. Also some of the costs seem a little unsettling, but I know those are based on BMW prices, I have to assume that there are people out there that are qualified to work on Minis besides dealerships. Anybody have any luck with this and can anyone calm some of my initial fears of the reliability issues? Also although I know that Mini had some real reliability issues in the first three years, it got better with the 05/06 models so I understand. Might this also be a reason for looking at an 06 as opposed to the redesigned model, where some issues might not have been uncovered yet?
4. Maintenance. I have to admit, I’m not the best when it comes to religiously maintaining vehicles, other than ensuring regular oil changes. I’m the kind of person that when the “Maintenance Required” reminder light comes on tends to ignore it until it goes off. Never had any real problems, driving the cars well past 100k. I know this kind of approach won’t work for a Mini, how much to expect in annual maintenance? Also are the $250 oil changes a myth or can the oil be changed at the local Jiffy Lube?
5. Lastly, got a question about a particular car I might be interested in. It’s an ’06 MC base—pretty much standard equipment, doesn’t look like it has many options—not even a moon roof (which doesn’t bother me, all the cars I’ve had in the last 15 years have had them, but I never use them). The car has about 8500 miles on it and offered at an Audi dealer for $16,900. The mileage and the price seem good, maybe even a little low. According to Carfax the car has a pretty clear history, one owner who had it for about 1 ½ years, two service reports, the last one being at the current dealership for an oil change.. Any thing in particular I should look for when inspecting the vehicle for possible purchase?

Sorry for the long winded questions, I guess I am trying to get some reassurance that a Mini is a good choice…I sure hope it is…thanks for your help!