I recently purchased a new 19’ Vintage Cruiser and towed it 750 miles home with my Grand Cherokee. The dealer installed a Blue Ox weight distribution hitch. It towed beautifully, not sure what the downside would be.
If you want easy access to beaches and shopping, traditional tourest area, Southern Maine is the place, we spend time at Wells, shopping in Ports mouth NH and Portland, Old Port area. If you want fantastic views, scenery, nice but hard to reach beach...
My homeowners/auto agent, Allstate, suggested I go elsewhere for RV coverage. I found Progressive and Good Sam were competitive so I went with Progressive (local agent). I recently filed a significant claim and the have been great so far.