Don't keep your boat in Newburyport if you actually want to use it. Reasons:
- Merrimack Current/Tide at Mouth is a PITA for Sailboats. Timing is everything. Ideal time to go out in is High Slack (either side) or Low Slack on Rising. All other times either excessive current or excessive waves. Any onshore wind wind causes standing waves at river mouth, no matter what the tide level is.
- It's almost 3 miles of slow motoring to mouth to Newburyport City Docks.
- Rt. 1A Bridge is tight underneath, especially if a strong current or wind.
- Can't really sail in the river. Either too shallow or too narrow, so first 40 and last 40 minutes of your sail time is you getting in and out of river.
I stored my boat up there for the winter last year and will never do it again. Boatyard was great, navigating that river wasn't. I missed the tide and was under a time constraint and went in on an out going tide near max flow. I had my Yanmar 27 HP motor full out and did 1 kt SOG for 20 minutes until I was through the jetty area. It took me almost 70 minutes to go 3 nm at close to full power.
My strong suggestion is to park your boat in Salem or Beverly Harbor and make the extra 25 minute drive from Newburyport. You'll never have a problem with strong current, tide or standing waves.
As far as 27-33 ft boats, I don't know of any that have "true" 2 cabins below. I think that you may have to go up to 36 for that. Also $50K is going to be tough for a boat that size (and of decent quality and shape with stuff) <10 years old.
I personally think that you should also consider a mid 80's Pearson either 33-2 or 34-1 ft boat or an Oday 34. Less than $50K, roomy, decent performers and solidly built. A well maintained one will hold it's value. A CS 36 could be a good boat too.
Older boats are basically done depreciating. Keep it maintained, and you can sell it for what you bought it for, or close, in a few years if the sailing thing doesn't work out.