Ah, why not just do a year walkabout and see how you get on? Rent house out, rent the tandem out (lol) and go somewhere cool. If you are worried about CV stuff, why not schedule in doing some MSF or other voluntary stuff when you are away- yes, you will be tied to one place for a month or two, but any trip needs a degree of planning.
You are right to be a little concerned about what it would be like if you just bunked off and sold everything- poverty with increasing age would not be a joke, especially if all you get is a 5th floor council flat in the banana flats in Leith! I suspect you know this, as as you say your 30’s involved re-building that aspect from a previous trip. Doing the same when you are 70? Good luck!
Dont rush in, take a sabbatical, be thankful that this is even an option! Good luck.