I am mostly concerned about his ability to afford the rent with a wife who isn't working and 2 kids.

Seems like everyone is concerned about cash flow (rightfully so), and therefore they go with a 30 year.

Family and friends are good way to start..some people it dnt work for cause of their friends being broke.

I'd like to save money but not if it's going to cause me headaches down the road. 

There's so many things that cause slow downs in areas.

I'm concerned.

If qualification if a concern, then perhaps a blanket loan would be better. 

Hello everyone on BP I've been walking with some people and interested in possibly doing the brrrr strategy my only concern being full time flipper how I go from hard money loan part to the conventional loan part if I don't have a proof of income.

cause the house is so small and the land so expensive in Westchester county.So does it make sense to just rent it out every year having someone else "pay" for the house?

You're at the 2% rule which is good......my concern is if it's a $20,000 property it is definitely in an "F" area so you may have some challenges regarding keeping good tenants, collecting rent....etc.