Most states allow you to hire your own adjustor to come up with your own damage amount and then argue with the insurance company about.The insurance company will want to see the signed lease, proof of funds the tenant paid and confirmation the utilities were on and preferably in the tenant's name.

., there's almost definitely significant value in some sort of proof of concept.

It's not fool-proof, but I think odds of earning 7.5% using a barbell strategy in the average year on your money is 97% likely with very very little effort. 

If you're living in it now, you'll probably be required to have a signed lease in place as well as proof that first month's rent/security deposit were collected in order to get a DSCR loan (they're business purpose loans and don't allow owner occupancy).

That first deal always hits different—it’s not just a property, it’s proof you’re making moves.

They have a system, team, and their own contracts, and also provide proof funds, even the EMD. 

Market Cycle and Seasonality7.

A savy agent sensing a situation like that might simply ask for proof of funds before showing the house which a nosey neighbor is unlikely to have.

If a tenant is constantly paying late and there seems to be a clear sign of struggle in finances, wouldn't I be doing a dis-service by offering the tenant to renew their lease and continue the vicious cycle?

What this also does is give me the chance to prove that its a good property, operate it to my written plan and present my 18 month historical financials as proof.