Back in the day I did many a night under a bridge with a bed roll.
I would think the life style is there if you want to live it for a time. Two lane roads and small towns.
I have always been a talker and even today when I pull into a small town gas station I have no issues striking up a conversion and getting warm feedback.
Plus you are on a Triumph. Everyone has a story and had one back it the day.
If it were me hitting the road today I would put a couple hundred bucks on a money card and see how long I could make it last getting odd jobs along the way.
Today I consider a Motel 6 or Howard Johnson's ruffing it for me.