To trailer or not?
Don''t get a trailerable boat for LIS. It''s too rough there and the boat will be too small anyway.
Get at least a 30'' sailboat and winter store it in a boatyard. The cost for winter storage is $27 at foot, mast in, where I store.
The wakes from motor boats is severe. The bigger boat will help some but some tactics are not to sail bouy to bouy and to turn up into a wake from the stern if under power. Wakes from the bow are just a bump and not that bad.
The trailer boat will fail to do the job on the sound. Even a big one will be too small in the end. However if you already have a 4WD and would tow it to other places for day sailing it would be ok I suppose.
In the end you are either going to own a 34'' + sailboat or give up. Keep this in mind. Buy or charter with this in mind. Bigger boats are easy to handle too. With just three people on our 30'' boat it was adequate for a long time. But a larger family needs more room.
So here is a rough budget. Winter storage $1000, Mooring at Noank $700, Insurance/registration $500. Now we get to "stuff" you want and need. You can see you need $3000 a year for a budget at least. If you go dockside then the cost goes up by a lot.