Jackson County TDR is working hard to position our area as a year-round destination, and it is catching on, but I wouldn't count on significant, year-round cash flow from a vacation rental here.

Start by analyzing cash flow and market demand for each property to decide which one to rent out.

.💰 The Cash Flow ConnectionThink about it - both investments are essentially money-making machines.

However, you have to be extremely careful financing 100% of the transaction as you still need reserves, closing costs, etc. and make sure it cash flows.You didn't mention if this would be a rental or owner occupied. 

@Shayan Sameerif you are putting down 20% cash but borrowing 80% from a HELOC, i still think you won't cash flow.i also get nervous when people throw out entire states. 

Your cash flow is positive on paper, but how will that look in reality?

I don’t have a loan on the property and hold it cash, but, if I sell it would lend the profits as hard money and earn 10%+. 

On my new builds we hit the double cash on cash in certain markets sometimes its only 50%.

Sounds like a cash out refinance would be the best way to tap into that equity. 

Such a situation is recoverable if there is enough time for a market recovery and the cash flow is at least break-even (or there is enough reserve cash to cover negative cash flow until it can turn positive).