I purchased a duplex in May of this year and moved into the bottom unit with the intention of renting the top unit as well as the sf I moved out of which would put me in positive cashflow (the top unit of the duplex does not cover the duplex mortgage entirely on its own). 

They "suddenly" look like geniuses 30 years later.1.

With that said, my goal with advance booking is to bring-in a decent amount of revenue during the offseason (winter), but don't want to scare anyone away with a large initial deposit, and of course I'd like to discourage cancellations.  

There are some good books that are low cost as well.

Andrew,i live in a rural location where the convenient store has the Post office attached/renting from them.i know the owner pretty well & can inquire)let you know. 

For instance, it may look like paying the $700 difference of renting your current property plus whatever your portion of the house hack would be (hopefully a significant amount less) and being similar to what you pay now or maybe a bit less depending on what you get for the house hack.

I am primarily looking for small multi-family and exploring cities in Ohio like Columbus, Dayton, and Cincinnati, as well as the RTP area in North Carolina.  

I think it might help some seasoned landlords answer your question if you share details about your rental like bed/bath count and sq ft.

As well as leveraging my knowledge on business.

I recommend going with turnkey deals in cashflowing markets that have a future like Columbus and growing your portfolio there.