I will also chime in...
1.) Is the Crossfire reliable? Absolutly! The Crossfire is little more than a rebadged Mercedes SLK320. The car itself has the Mercedes workhorse engine the M112 engine. As a whole the car if maintained is going to last you.

2.) If you follow the on board computer oil changes will occur around 7,500 miles. Use top quality oil such as Mobil One. If you use the search function you can find a wealth of information. The cup holder is an aesthetic concern. The standard cupholder has somewhat of an eagle claw effect. It will in effect puncture what ever is put in it; lol.

3.) In the price range of 8-12k you will find a wide variance of Crossfires. Just inspect the car or see if a fellow forum member can check the car out. The best case scenario would be buying a member's car, check out the link for Private Cars for sale:
Private - Cars For Sale

4.) I have only test driven the manual, and realized it would not be a good fit personally. I have a failed ACL reconstruction in my left knee and I didn't think I would enjoy driving the car. I would say test drive a manual. Prior to test driving do some research on the forum in regard to the manuals on these cars. The auto stick is a good autostick. You have to remember these cars are utilizing technology from first part of the last decade (late 90's to early 2000s). With that in mind a great auto, put a Sprint Booster on it and the shifts are firmer and the transmissions responds faster.

5.) There are quite a few members who drive the Crossfire as a daily driver and long trips. More than one has driven from PA to TN, Canada to TN, ect. The Crossfire does take some time to find your personal sweet spot seating position wise. Once you find that sweet spot; they are great cruisers.

Roominess wise I am 5'11'' and weigh 260. I do not have any issues what so ever. There are guys who are much heavier and taller than I am and they use their cars on a regular basis.

6.) Again, these are Mercedes. I have never had a problem with the heat or A/C being

7.)I can only answer this in regard to an automatic limited models. The NA Limited cars do have Cruise Control. As a whole in comparison to a Pickup and Conversion van you will find yourself grinning.

You note you have a history of working on cars. What is great about the forum is members since the forum was founded have posted Service Manuals, Tech Bulletins, and other maintenance related posted (See link)https://www.crossfireforum.org/forum...ollection.html
If you have a laptop or printer, can read, and turn a wrench you can do most of the general maintenance on these cars.

There are some performance mods for the NA, but its not a V-8. Rob at Needswings (Product Category Listing) and the guys at Eurocharged (N/A) have proven performance mods for the NA Crossfire. I believe rear wheel HP for the NA can push 195 HP+ for the highly modded.

Hope this helps you in your search and you stick around.

Jason