Newbie Introduction-Airbnb house hack???

[Michael Kelley]

Hello Everyone!

My name is Michael Kelley, from Bardstown, KY (about 45 minutes south of Louisville). I am new to the real estate investing world (currently no deals have been made), but I have been reading, listening to podcasts, and trying to learn from others around me. Right now my interests are in BRRRR to build net worth, with the hopes of rolling over, via a 1031, into multifamily down the road. I also like the idea of flipping a few homes alongside brrrring for some additional short term cash, and the two seem to to be fairly similar as brrrring is practically flipping a house to rent.

The primary thing holding me back from investing is that I do not have my own place yet. I really want a place of my own, but do not want the major liability, therefore, I am looking to house hack my way into my first home. Right now I am looking at a vacant lot just outside of downtown Bardstown, it is not the most ideal location, but compared to other homes with similar distances from town I can still expect decent bookings to offset, and possibly cover, my mortgage.

The catch is that I want to have two separate spaces, one for myself and one for the Airbnb; this is both a personal preference and "entire place" rentals tend to do better than shared spaces. However, I am afraid having two separate kitchens and living spaces will be hard to sell whenever I decide to move on to bigger and better. The current zoning does not allow for a duplex, so it could only be sold as a single family home or a short term rental investment property. Another option would be to build a small single family with a detached apartment garage to be used for the Airbnb, but I am afraid that will cost more than what the surrounding homes are worth.

I was hoping to get some feedback from the Bigger Pockets community. I feel as if I am going into analysis paralysis and I am torn on what to do. Should I go for it, or try another route? Any help is greatly appreciated!