An architect will be able to answer those questions and perhaps be able to identify other physical and economic obstacles that won't arise when merely approaching this through the lens of whether you can obtain a zoning permit.

Go visit all the other new/newer buildings around there to see what amenities they offer like dog washes/automation/business centers/fitness centers/package lockers/etc and compare the rents.   

Both of those towns have stringent rules about STR's that can make it more difficult to find the right property that will fit your strategy.

However, after a successful first wholesale deal, I realized wholesaling wasn't the right fit for me and I took a break from real estate to explore other opportunities.I'm now excited to dive back into real estate investing and am eager to network with other investors and real estate professionals in the area.

Each to their own like you say but appreciation is where the money is made in (finite) and (physical) assets.

Buyers are now responsible for ensuring their agent’s compensation up front before showings take place.When you meet your next agent, consider suggesting a meeting to determine if you’re a good fit for each other.

Yes I pay more for her (around $10/hr) but you get what you pay for.If people message me happy to provide company name, what they do is they find the VA's and have them take Culture Index and other tests and they prescreen them, then you interview them and select the best fit

If aren’t by able to find a suitable means before month 1 ends and your booking cancelation timeline then maybe you let them stay, but seeking someone who understands that offer or it perfectly fits could be a win win for you and them.

Multifamily DSCR Loans (https://www.biggerpockets.com/blog/multifamily-dscr-loans) would likely be a perfect fit for this but unfortunately are pretty much always capped at 10 units...

Cincinnati (maybe Northern Ky too) I think should fit your preferences well.