Even though we were nor in tourist place, house seems almost more than 50% occupancy rate except winter. ( In winter we had mid term tenants)  However, even though our property is popular, because we pay a lot in mortgage, many times it is negative cash flow and pool seems constantly leaking.

With about 100k to put  down, I don't think I can be anywhere close to cash flow break even (at least not in any market that is driving distance from the Metro DC area). 

If you're maxed out on retirement accounts have you looked into cash value whole life insurance?

It's a cash payment, no reversals, instant transfer to your Cash App account. 

Experienced investors with plenty of cash Millions in Cash will get them.

Small markets with a good amount of cash transactions.

Other advantages besides cash flow are the appreciation depreciation and tax write offs.

Financial risks, such as unexpected repairs or vacancies, can also impact your cash flow.

After a cash-out refi, I had my money back.

If it's not cash-flowing why not sell?