I am not a tax professional and the RE in question is commercial real estate so certainly not my realm of expertise at all, but if OP has residential mortgages in their future (personal residence, etc) this would look highly unusual.

I would credit their rent each month a static amount, that would represent my usage.As far as the initial 3 months of the month-to-month lease, I am uncertain how to share the utilities.

I recently purchased my first property and am going to begin house-hacking in the next couple weeks. Once my inherited tenants have moved out, I'll be moving in and placing new tenants in the unoccupied unit. Outside ...

But if there's a pattern and if all the other neighbors also call continuously, then you can get a call sheet after a month or so and see an unusually high number of police calls. 

It's not unusual for a landlord to not be forthcoming with a tenant they were happy to get rid of. 

To be honest we are still uncertain as to the extent of the loss especially if there is a second wave.

Hi All,I want to see if this unusual property I am considering purchasing will rent and at the price I need to it to cash flow.

We are in a hurry to make real time decisions to requests, but saying you will double check and revert back can avoid uncertain decisions.Hold tenant deposits in a separate account even if you just have 1 property.

It sucks you were burned from contractors, who perhaps took advantage of the uncertain nature of covid, but I can say from experience that getting burned is the best way to learn!

Our L/O offering was unusual in that most owners/landlords using L/O before 2010 saw it like you do as a revenue enhancement tool rather than a 'normal' alternative financing method.