Move-in, mid-lease, renewal/move-out, plus any other time we have severe weather or other concerns relative to the property's conditions and maintenance. 

In any case there is no taxable event yet.As far as your brother is concerned, it again depends on the nature of the transaction. 

What are the concerns?

Most tax professionals do not advise their clients to utilize this approach and it may raise concerns under IRS examination.

Meanwhile, your expenses, like debt service, taxes, insurance, and maintenance, continue.Another concern with investing in disaster-prone areas is the high cost of insurance.

If it is/was an automotive repair business I'd be concerned about underground storage tanks, surface contamination, etc. 

Never talk about being an agent unless the question explicitly concerns that.

That was actually my concern, getting the type of tenant that don't destroy the property.

But each little area has a rule concerning short term rentals.  

If you’re focusing on specific property types (single-family, multifamily, or fix and flips), I’d be happy to help analyze the financials of the deals, without any concern about me sniping any good ones you find for myself, haha.Let me know how I can assist!