I know they’re an essential tool for analyzing a property’s financial performance, but I want to ensure I’m approaching them correctly.Could anyone share examples of what a good T-12 looks like or highlight key items I should make sure are always included?

Ensure the sublease is explicitly permitted in a written agreement with your friend and aligns with local STR laws.

It is YOUR money and YOUR investment so ensure you do YOUR due diligence.

* What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuits* How familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?

Also, in regards to a per diem, I'd like to be a bit more optimistic that I can establish the right checks and balances to ensure that the contractor is not skipping corners.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

I would just take into account that a lower down payment will mean a higher monthly payment so be sure to run the numbers conservatively in order to ensure your STR revenue is able to carry your monthly payment with this higher mortgage cost. 

I've done plenty of deals without and agent, off market not even on the MLS but I'm one of those wholesalers that did things properly, had qualified buyers before even reaching out to sellers and strictly stuck with assignments.Biggest problem is so many "wholesalers" barely have the understand of a deed or what title insurance is so there's an immense amount of knowledge they need before hand which can just be provided to them by getting a license!

His focus was on location, tenant demand, and ensuring the property could handle at least a 1.25 DSCR even in a downturn.

I am orginally from Elgin, but living down in Logan Square area of Chicago proper!