Having spent a summer boating on the lower Hudson as a kid, I can say that it gets fairly boring. I grew up there, although, our boat was normally on LI Sound. You go north or south, south or north, a little of both. Same thing every time. In Albany, the river is very narrow, so all the more limiting. Barge traffic is also a PITA when sailing, they have ROW.
I would get a trailer sailer. The lakes are much closer than you think and there are many. Sailing out to one of the islands on Lake George and camping for the weekend is great. Lake Champlain is not really that far either. You might research launch sites to be sure that isn't frustrating. You can always drop her in the Hudson after work during the week to get a quick fix.
Since yyou will sail in fairly small places, I would focus entirely on ease of launching/rigging over performance. A 19 ft ComPac with articulating mast would be perfect IMHO. I want one for the lake near my home. I'm just sane enough not to have two boats!
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.