Alternatively, if I left the unit as is, or added a bedroom for a much smaller cost by removing the dining room, I could rent the entire unit out on a short or medium term basis, for at or above the monthly cost, then look for a separate house hack with a bath already installed.

Also, setting up one of the units as a medium term or short term rental to increase income.

Quote from @Khail Towers: Just bought my first rental property (1 bedroom condo) in the Walnut Creek, California area (SF Bay Area).I've decided I'd like to rent the condo as a medium term rental (MTR) to travel nurses, corporate housing, etc, but I have no idea how this works.Do I just go to hospitals and let them know I have a condo for rent? 

There is a decorative grate you can put over that but I don't think they make it baseboard insert width. 

At some point in the near future I will sell everything (small to medium properties in the $300K - $7M) and do a 1031 exchange (so I don't get slammed with taxes) into a handful of large income producing properties...hire a management company and call it a day.

My wife and I are pre-approved for a home and have been considering house-hacking a multifamily in the Poughkeepsie area; potentially focusing on medium term rentals for traveling nurses.

If you want to attract high-income earners who are used to a certain quality of life and can't afford to buy in those areas, then look at your available options; house-hack, partner, buy a condo/townhouse as opposed to a single-family home, start with medium-income earners, etc.

Right now it is staying profitable as a short term, but hoping it will work as a medium term for more stability and less stress!

Honestly you’re not gonna cash flow pretty much anywhere in the region and to be honest you can “house hack” a rental basically you could rent a room in a house, the biggest reason to buy is over time, the appreciation plus locked in payment looks better over time, frankly that time horizon is about 5 years on average right now, if you expect to be in the region for the next 5+ years buy something I’d probably prioritize buying something your comfortable in for the medium term than “cash flow” which your not gonna find regardless with these rates. 

My particular interests lie in the buy-and-hold market, as I'm looking to own both short- and medium-term rentals.