You will hire 2-3 of the wrong contractors also and lose 10-15k in walkway money.Your first try should be to do a flip as a smaller partner with someone else, a friend, a local investor from a meetup, so you can learn the ropes, know how to manage a crew, etc.

I have seen plenty of investors getting burned buying homes in very attractive locations only to find out it is not zoned for STR and ending up losing $$ getting rid of the property.

Even to the point they lose equity disproportionate to the LP.  6.  

You lose the money and then work.

If you have negative cash flow, you are losing money.

His case worker should be able to talk to him because he's going to be at risk of losing his section 8 support if he can't follow the rules. 

To me the bigger risk, and more highly likely to happen, is to be heavily leveraged and then something happens such as a big downturn or covid and you don't get rent for 6 months or more and you can't pay your mortgages and you then lose the property to the bank.

If you don’t have the cash and don’t have a preapproval or commitment from a private money or hard money lender but you are making cash offers, that’s an issue because you either can’t close or your going to lose your EMD and waste a lot of time.

It is still okay to lose money every month!!!

You would be better off having two properties at 50% leverage than one at 0%.3) You lose out on appreciation benefits by having one property unleveraged when you could have four properties at 75% leveraged4) Unleveraged properties are a target for ambulance-chasing lawyers and also now fraud.