I have found a screaming deal on a residential condo, but the problem is that the master dec states that it cannot be used as accommodations or residence.It is in a resort area and the highest and best use is nightly vacation rentals (VRBO, Airbnb, etc.). 

If you're renting to them without a valid lease, that is, on a month to month basis, I think you should give them the month's notice required by NY Tenant Law, stating that that you are vacating the apartment for renovations after which there will be a substantial rent increase to fair market value.

They wish to use it as a weekly rental for reunions and vacations.

Something has to pay the bills, put food on the table and yes, cover health costs.Building your wealth by doing RE might take longer than expected.Here is a quick example:A mid-level SW engineer in the DFW area makes about 100K / year plus bonus (about 10%) plus 401K matching plus benefits (health, dental, vision) plus paid vacation days. if you sum it all up, about 140K total comp. 

I have a vacation rental on a small lake.  

I'm an airline pilot and I can hook you and your family up with some free tickets to a nice beach vacation down here in Florida where my family lives.

All it needs is mattresses and a kitchen table and it could rent out very profitably as a short-term vacation rental. 

Hello fellow investors,As the topic states, I have decided to take the leap and I would like to invest in a piece of property that will be a vacation/rental piece.

Top of the food chain - stroke his ego.If he does need some cash upfront as a good faith or vacation, etc. offer him a small down payment.

I live in a town where vacation rentals are quite popular and I am interested in getting a few over the next few years.