I am also a member/subscriber of Vodessey, Short Sale Prophets Basic, and several others. 

I'd like to know your thoughts/advice on how to compare long-term and mid-term rentals.

https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

Projected sale: 950-990k Replacement property budget: 990k - 1.1M Plan: rent out the replacement home until meeting the requirements, then move into it while renting out a portion of the home via short-term rental 

Of the many strategies I've looked into, House-hacking and short-term rentals piqued my interests. 

come on now.. we all know these are fake lenders.. its simply not real.longer term fully doc  sure.. 

I'd underwrite the property, with that low interest rate assumable mortgage, to cash flow positively from day 1 as a long-term rental, but be willing and able to use the rent by the room strategy or to rent out part of the property as a Short Term Rental to dramatically increase cash flow during my occupancy. 

Short of coming here and meeting face to face with them and come to a couple local REIA events to discuss, for those who are remote I would suggest getting into some of the NE Ohio REIA facebook groups to get some advice from locals.   

If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

Focus on long-term guests, like corporate clients staying 30+ days, because it’s easier and brings steady income.