having sailed all over the ches since the mid 60's, here's what i think..
of course first question is where "near the bay" are you?..where will your cruising grounds be for the most part?
also, what kind of sailing will you do..any racing, or mostly cruising stuff?
what/where will you keep her?..as in budget for marina per month..
based on what i'm gleaning, you might want to look at a sabre 34 with a k/cb config..make sure you get the centerboard checked out/ serviced, sooner than later..this will give you 4'3", board full up (iirc) some decent ones out there in your range..most will need some tlc and elbone grease
i am a sabre appreciator, 2 in my immediate family. '84 34' and my '90 30'
if length is no object, some really rough late 70's early 80's tartan 37s can be had..but most are "rode hard put away wet.."..if you are handy, and can do most of the cosmetic work yourself, this is a great bay boat..they are exceptionally well made cruisers...pearson..erikson and of course the c&c's are worth a look.
so..where did ya say you were gonna sail..i do know some decent brokers..scott vail in irvington, and brett or barry starke in oxford..all are great guys..know the bay and are stand-up folks, all.
i bought my J/24 and sabre through scott...tred-avon yacht brokers (barry and brett), graciously spent lots of time w/ me and directed me towards, and away from some boats..
if you are north bay, give em a call..southern..scott's your man.