Don't knock the instructor route. It's way better than doing no flying at all - it'll keep you current, build hours (may be not the best hours, but better than staying stuck at 285 total). It will also help keep you in the network - the single most important factor in getting that first job. Most flying & gliding clubs are frequented by airline pilots - get to know them!
I spent many years as an instructor in the recession-laden early 90s. And every job I've had since then has been through contacts, not mass CV mailings (but do that too!). I got my first airline job with 1500 hours, almost all instructing hours in C152, PA28 etc. It's still much better than 285 total & no longer current.