Once you do this conversion you can't change it back to a traditional long-term rental. 

Cash flow is definitely the biggest challenge; both in terms of finding properties to buy that cash flow with a loan on them and just company wide given interest rates and labor/material is up and, at least where I'm at in Jackson County, MO, taxes are way up too. 

It can be a positive for short term rentals (if in a good area) to be near the airport.

Everybody is different, some people like flipping, some like short term rentals, some like long term rentals. 

That’s the magic of real estate compounding over time, and it’s stories like yours that really highlight this.. from what i read in the street journal, that slow build often outperforms shorter-term stategies.From an investor-friendly agent’s perspective, being willing to dig into the neighborhoods (driving for dollars) and having a robust network.. from probate attorneys to local contractors.. can pay off big.

In terms of appreciation as well.

I have one long term partnership that we share capital but I still do all the work ( rain maker) he is a cpa so he does do the books and tax return though :)  WE built one subdivision together were he put in 500k and I made him 1.2 mil in 18 months net profit so that was not bad.

Will I be able to overcome it's reputation in getting mid term renters?

With countless loan options, complex terms, and strict lending criteria, it’s easy to feel overwhelmed.

I primarily invest in buy and holds, but I do a little bit of everything including fix and flips, airbnb's, mid-term rentals, and wholesaling.