Just listened to the Bloomberg Masters In Business podcast episode with Len Keifer of Freddie Mac.

Finnegan I'm in agreement with @Greg Dickerson you could always do a master lease agreement. watch this vide to get a better understanding of what one is. https://www.youtube.com/watch?

For total expenditures of $1,901/month the units rent as follows1 bed $7001 bed detached unit 2 bed unit with a huge second floor master $1,050Total income $2,450 - each unit is about $150 under market, total $450 under market.

I've checked my master meter and the meter did not move (slow flowing dial). 

Don said it best, But ultimately you want to connect with  legal counsel in your area  that's familiar with real estate and short-term rentals  as  Master leasing might be a great way for you to get in without invest your money  to begin your portfolio first to build credibility

-Put new hardwoods down-Installed the new kitchen and poured a 10'x6' concrete countertop for the island (I think my back still hurts from mixing that concrete)-Replaced the stairs with new treads, risers, handrails, and picketts-Opened up the back two bedrooms upstairs to make one master suite with walk in closet and master bathroom-Installed stackable washer/dryer outside of the master-Opened up the ceilings in the front two bedrooms to be 11.5' tall.

Thinking of finishing off the basement to include a master suite (1bdrm+full bath) as well as a decent size entertainment/living area.

If you give it a try, be patient and don't get too excited about moving into the new neighborhood and buying there for at least a couple years , so you can make sure you have rental ownership mastered.   :-)

I personally finished my masters degree and was well established in a career before I made the switch to being an agent.

Was it the market aspect that took a while to master?