Want My First Bike

[V1GiLaNtE]

You picked peak times to buy a bike. With that being said:

SV650 - 2nd gen if you want FI (05+) otherwise the carb ones are just fine too
GS500 - Joey had one. Cheap all day
Honda VFR - Good sports touring and dead nuts reliable
CB600f - 4 banger SV
Ninja 650r
Dr650
KLR650

Lastly, I am thinking the power range of 500-600cc will be best as 250 will be too low for me to be satisfied for more than a few months, and I think a 15-20 year old 600 will be enough power to keep a smile on my face without my smile ending up on a guardrail somewhere. 

250 is plenty of power to get into trouble with. Yea you're not gonna be stunnin' em on the straights, but hang off the bike and throw it hard into the twisties and you'll be pulling back on the power. Unless your goal is to simply cruise and look cool. If you're interested in actually learning how to ride, I'd say just buy a 250 for the summer months and then dump it in the fall. Save that and money over the winter and pick up something around February. Your first bike you have to be completely comfortable knowing that you may have to write it off completely.


Edit:
You should also be factoring the cost of gear into your bike purchase.