I'd keep checking back on the OTLA website here: https://dhcd.maryland.gov/Tenant-Landlord-Affairs/Pages/defa...

It's always better to check with your brother's CPA since he has all the background, but I would say short-term rental with material participation requirements met by your brother, then do cost segregation.

You might want to check if your PM also covers areas in Cleveland since you're already comfortable using them.

Most standard leases have check, or cash as options as a default so tell him that's his only options if he doesn't want to pay that way then he has to move on with a loss of his deposit.  

Last time I checked only people who have lost a home are those who do not pay.

So I told my tenants I wanted to switch to RentRedi for payments because it was more streamlined than collecting checks and such but then they would be forced to pay the $1 transfer fee.

I wanted to check the calculations that are presented in James Dainard's book, The House Flipping Framework: The Tactical Playbook to Scale your Real Estate Portfolio and Reinvest your Profits.

I recommend a simple spreadsheet to check your math and it will make it simple to adjust each year.End the complaints.

Seeking advice here on the best approach, any gotcha's that I'm missing, and overall sanity check... 

Do you check Landlord references?