I agree with Samicat. At 49 when asked what he does for a living, I’d expect a specific answer I am a welder working for XYZ company that makes ornate gates or , I am a property manager in XYZ company that manages condominiums. Vague answers like what property he manages (his? Someone else’s? Manages how? He doesn’t actually have a job?) and odd random jobs at 49 are strange. Driving puppies?

It might not be as much about money as it’s about unstable life style at his age. He’s going to sail for 10 days? He has ten days vacations from work? It kind of points out that perhaps he has no full time job. So no health insurance then either?

I’d google him and see what pops up. You’d be surprised what you can find by simple internet search. I once had a bad feeling about a man and oh the stuff I found. I couldn’t even believe you can find stuff like that by simply typing a name.