[Build Help] Couple questions about upgrade

First of all thanks in advance for all the help, this subreddit is just amazing. Currently my rig is based on a q8400@3.2ghz, 4gb of ddr2 ram and a 250gts 512mb in an 720p HDTV. I'm preatty happy with its performance but lately I started to think in an upgrade, but by now I have only U$200.00.Now the questions: 1-Should I buy a 1080p monitor like 23'(inside my price range) or stick with my monitor? 2- If instead of buying a new monitor and buy a GPU, what would I need to max games in that resolution?(I believe that in that res I'd be able to do it with my money). Also I have a 600W PSU that should handle any GPU in this kind of entry level segment. 3- Would you recommend a SSD of like 30gb for boot drive and chrome or would I need 60gb at least?

My current plan is to keep the monitor, but you guys can convince me othereise, and buy either an 7850 or an 7770+30gb SSD.

Tl;Dr 200budget,720p tv as monitor, 250 gts. What should I do?