I have been assuming that warm climate means Caribbean
I noticed on another thread slip fees
are quite steep down there. That would have to be " feathered out".
But there is no way anyone would be willing to look after such an endeavour
with out being reimbursed some how. I don't think an hourly wage would be the way, probably salary.
Maybe even more important is to have living arrangements ironed out.
But all of the above would come out of membership fees
. Keeping in mind if one bareboats for 5 to 7 days the cost starts at $ 3,000.