I would consider cruising the Ranger to FL to keep it or selling it up north and buying a used but larger trawler down south for less money. I'd resist the temptation to cruise to FL then sell due to deflated boat prices there. Sell up north and drive to FL to buy your new dreamboat...not necessarily a N37.
Rangers are nice, but their prime attraction is their trailerability. That's got to be worth a premium if you sell it up north. Then you'll have a pocket full of cash to spend on your next boat without going into debt. There are a lot of boats in the 35-40 ft range for what you can get for you Ranger 27...they just won't be as new.
Retirement spending is a whole lot more fun when you have money in the bank. Driving up debt in retirement is not a good idea, IMO. We bought our boat 5 years before retirement to try it out and if we liked it, fix it up to our preference for retirement. We did this while we still had loads of disposable income during employment. We retired 2 years ago and have been enjoying the boat in its improved state without having to foot the bills of improvement on our retirement income.
There are loads of folks out there who have done the same thing with their dreamboat in retirement and now are looking to move on to something less demanding that cruising. Those cherry boats are out there for the picking. I would think FL is a target rich environment for anyone looking for a boat to buy.