Your decision to lease this property for short periods is what makes this a short term rental property, not the property itself.

Considering selling a home for short-term rental (STR).

This one will cash flow a little when we move out but it was a bit more of a long term play for us (5-10) years, so we need the time to make it worth it.

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.

Still, I think you'd find it difficult to find one that would be a good long-term investment unless you had another ~20-30 years to go, it's at least cash neutral, and you don't plan to hold it too long (to avoid too much investment loss and before you get to the point where it's unsellable because of too few years left); that's another way of saying that maybe it suits your cash needs in the near-term or is at least less of a pill to swallow than other options until you find something that's more of a sensible long-term play

I’m holding for the long term.

I am bullish on Chicago long-term and will still own 10,000 doors on the southside with a goal of turning all 10,000 tenants into homeowners!

Whether you choose short-term or long-term rentals, learning and analyzing deals will help you make the best decision.

I’m considering buying a plot of land in the Cleveland area and getting a manufactured home (duplex if I could find the right zoning) put onto a permanent foundation to use as a long term rental. 

Syndications are great for truly passive income, offering tax benefits and diversification, but require high minimum investments and long-term commitments.