Most watches are easy to sell IMHO. I've bought and sold a bunch of watches. Do yourself a favor and buy used (it appears that you're trying to go that route). I've sold a Panerai, Rolexs, Omega and U-Boat.
I know you're not a "Rolex" guy, but that is the watch that I either lost the least on or actually sold for more than I paid for it. So if you're interested in a watch that will recoup or be the easiest to sell, then it's for sure a Rolex. I wore a Submariner Date for 10 years and sold it for $800 more than I paid for it. An older Submariner or GMT II will easily go with a suit or jeans. The pic is of my GMT II Pepsi.
Here's a nice Sub for sale:
http://forums.watchnet.com/index.php...o=708276&rid=0
You can get the GMT II in an all black bezel, black and red or blue and red bezel. The older models you can actually swithc the colored bezels pretty easily to have a different look of the watch.
http://www.watchrecon.com/?query=rolex+gmt
If you do go for a used Rolex, make sure it has the paperwork at the very least. You pay a little more, but in the end, you'll make out better down the road.
That being said, it appears you're interested in the Tag Carrera chrono. VERY nice watch, but make sure you buy it at the right price. New you'll never come close to getting your money back. A few of my buddies have them and have never had an issue with them.
If you dig hard enough, I imagine you'll find people who have had problems with every watch brand. I have friends that have had horror stories with Breitling and Cartier. Others have had no issues at all. I have a Bell & Ross BR01-92 that needs service already since it's losing time at a rate of 2-3 minutes a week. My Submariner that I had I never seviced it in 10 years and was running very well.
Make sure you go to a watch store (like Tourneau) to try on the model watch you want. It may not be what you expect vs. just seeing it in pics. I LOVED the Panerai 177 because it was brushed titanium. Hated it when I tried it on (too light) and ended up getting a 111.
Get what you like and you'll enjoy it more.