I've had some not happy when I have asked them to split it out.I've tried asking questions to the IRS customer service reps, and didn't have the best luck.While I cannot cite a specific official guidance on this issue, I consider debit cards exempt.

I read this as someone using a short-term lens to focus on a long-term issue. 

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

The issue I see is smart contracts/tokenized real estate and traditional real estate investors is like oil and water.

My manger does this all the time.He has an inspection done to verify all the maintenance issue and has someone video the property to verify all the marketing issues.

Or this is a non issue if insurance coverage is not taxable.Many other thoughts and input.

They might only skim an inspection report and trust me to find issues.

@Jesse Rivera I love the idea of it the only issue I'm currently facing is I would get negative cash flow renting out my current home  based on my current mortgage so it definitely isn't ideal 

The inspection showed more issues than we expected but the seller wasn't willing to negotiate so we cancelled in the due diligence period.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.