1000 TT / 100 ME will make you competetive for the better regionals. If you can save money AND build flight time I'd probably do it.

If you're working at or near any of the large US military airfields in Germany you should have access to a military flying club, which will be a lot cheaper than European general aviation. Check into that, and also find out if contractors can use the flying club. Military and DoD civilians can, and I think most MWR privileges are extended to contractors serving overseas.

Also, CFI's at military clubs do not need MWR privileges...they automatically get the privilege because they are considered a DoD civilian employee of sorts. If you have or can get a CFI, you can probably do that part time at the club. They are usually short staffed, at least in the states.