I know in theory the process of BRRR, Buy & Flip, Buy & Hold, et... but I am very worried about screwing it up and really putting myself and my family in the hole ( I have a wife and a 1 year old son).

If you are ever forced to sell you are very likely screwed.

Please tell me how I screw the landlord? 

You won’t be doing any background check on anybody living in your property, that’s for the person screwing you to do.

Yes, you can do a cost segregation study in a year after the property is placed into service.However, you will need to file a form 3115 which basically says you screwed up the depreciation in the past and as a result recalculating the depreciation.

They do not communicate once you’ve informed them of how they screwed up.

I know in theory the process of BRRR, Buy & Flip, Buy & Hold, et... but I am very worried about screwing it up and really putting myself and my family in the hole ( I have a wife and a 1 year old son).

Your challenges:1) Finding deals2) Understanding what makes it a deal and how you can profit3) Learning how to properly wholesale, so you don't get screwed by a seller or another investor-buyer.

Screw it up and you could lose the investment and your relationships.You need a contract that clearly spells out what each person is investing and what they will get out of it.

I could list countless scenarios where a lender seemingly screwed a borrower/investor over, either by design, or unintentionally.