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. 

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). 

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.

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).

Since your lease doesn't include a break clause, you'll want to communicate openly and give them ample notice, ideally a few months.

Our priorities in terms of market is there needs to be- anticipated economic growth (lots of tech companies are moving into Columbus),- prices need to allow us to buy in all cash (400k or less, ideally up to 300k),- we want the area to be safe (when looking into places like Dayton, OH or Memphis, TN for instance it looks like all our boxes are checked on paper, numbers wise but we realized quickly there are a lot of unsafe areas and we could have the potential for problem tenants)- yearly expenses to be relatively low (i.e. we are avoiding NYC and the tri state area, California, etc. for having extremely high taxes).Is our initial analysis on the right track for Columbus?

We project we would still be cash flow positive even with the extra costs of the HELOC, but we would ideally rather have more cash flow then less at this timeWhat are things we need to be considering or thinking about?

Now LL are stuck with these less than ideal tenants.  

The property's market conditions and location in Stockton made it an ideal candidate for a fast resale, aligning perfectly with our investment strategy.