I am an interior condo/house renovation contractor from NY transitioning to a rental property investor.

Assuming it will need to be owner-occupied to STR, if I need to move out within 2-5 years I’d transition to MTR or LTR.

I can tell you I've had quite a few owners calling me in the last few months looking to transition their STR into LTR for the same reason, and like you, many are stuck. 

Overall the project went smooth, just some problems along the way.

Here are a few additional considerations and elements that you might want to include to ensure a smooth and legally sound transaction.

These loans allow borrowers to pay only the interest on the loan for a set period, usually the first few years, before transitioning to paying both principal and interest.

.: Insulation, or lack thereof.Just ran into this one and it really surprised me, but I guess the transition from floor fan to window air conditioner to central air were all upgrades to a better way of living and that pesky outer wall insulation was an expense that just didnt make any sense back then.Energy efficiency???

I am working both with the owner of the company and an attorney who is a family friend to make the transition over the next few months to adequately learn the business and processes.

Examine if the current state of the market is conducive to investing.Local Amenities and Infrastructure: Take into account the accessibility of schools, public transit, and other infrastructure as well as amenities.

After that, I stopped flipping and fully transitioned into wholesaling only.