I guess it is okay. I am not sure that SS has alot of young yuppies like you are saying but it may not be bad for you. There are a fair share of engineers that rent in SS and the likes who work at some of the larger firms like Broadcom up in RB. If you have rented in 4S for awhile it sounds like you know the area fairly well. Also you definitely will not be surrounded by college students like you would be if you got a place in UTC. You can also find places in the 200-300k range like you are looking for but I am not a huge fan of renting a room out of my own home out of necessity to pay the mortgage. Seems like that can end badly. Unless you are doing it right now it is a change of lifestyle that most often does not end well according to what I have heard. You may want to consider Scripps as well. For what you are looking for PQ is not that large. It is varied though.
Anyways I think it is a fair enough choice. If you wait awhile you may be able to catch some better pricing.