As there is no cashflow during this period this may not be an ideal scenario for everyone but we are all cash buyers building out a portfolio that will provide income to keep our current living standards once we retire from our day jobs in 5-10 years. 

He wasn't able to write new business but was doing a fine job taking care of his current customers.

A higher cash flow market would certainly be ideal, but I wouldn't go for a "cheap market" (which sounds like a high crime, blight-filled, declining city). 

Some think they do but they really don’t, they need a lot of guidance and hand-holding that the listing agent can’t provide them as a customer or a transaction broker. 

Ideally, I would like to buy in the Catskills since it’s close by, a popular year round destination from the city and has a history of vacation rentals but I know there’s more and more talks of regulations so I am open to other areas and would love to hear your thoughts/experience on the area.Would love to connect with anyone who has interest in the area and the short term world as well as agents familiar with STR who could help us in our search.

@Sai Kumar we work with a lot of real estate investors in FL and have good intel from customers on PMs with great performance and reasonable fees.

Selling to investors at a fraction of its worth is not ideal, so I'm looking for alternative solutions.

And ideally sell it 4 years later.If I can more or less count on the renting of additional bedrooms to cover the running costs of the house, I'm really only looking at taking a hit on the buying/selling costs - which SHOULD be lower than what it would cost to house him in dorms for 4 years.I feel like this is pretty obvious and easy (not trying to make significant money here, just thinking I could save $10-$20k on housing costs over 4 years).

This is pretty bad customer support!

Every business looks at how they can increase what a customer spends.