Boat US will require a haul out survey by one of their approved surveyors.
Progressive will offer liability w/out haul out but premiums are higher.
Boat US offers towing as does towboat , you'll want to check availbility of these services in the area's you will travel.
As to stepping mast,it is very simple and straight forward. You can do-it yourself at Castleton-on-the-hudson boat club for $50.00 there are usually plenty of people around that will help if you ask (other's doing the same,waiting for you !) Also it is a GREAT place to stop after leaving waterford (where you must stop for at least the evening) and the distance is right for making it to Castleton. At castleton you can dock for $1 a foot and they have rest.bar,showers,and laundry within walking,small stores for light provisioning etc. Also a moring ball for $5.00 if you prefer and dinghy
in. It's a must stop IMO.
This stop also sets you up for stopping along the way at anchorage spots south. I'd have to check my log book for the other anchorages I've used.
You would be wise to use the tides to your advantage,it goes better.
I often anchor
just north of the bridge at Tarrytown and dinghy
in to the park/ballfield if I need to go ashore. From there I usually stop West of the statute of liberty on the jersey side and anchor
next to the state park,you can pull right up to the launch ramp if you want,but I wouldn't, I just anchor
in. If weather is poor it's a good spot to wait it out.there is a diner 1/2 block walk.
I'll check the log for other spots I've anchored or docked for free.