In a perfect world everyone you hire would give you a written quote on company letter head spelling out the scope of work, estimated cost, obtain the materials on your behalf, bring all their own equipment to the job site, show that they are registered and bonded in the municipality where the work is being done, and pull the permits.

@Dominick Marschall another option would be to do a cash-out refinance of the property and pull out some cash.

A written lease should contain a "both parties agree that any/all other or previous or outside agreements are void" clause, that you could then show to a judge if the tenant pulls out an audio recording of a rent to own agreement with the previous owner (gotta be a bit paranoid when it's a $500k asset on the line).

I have friends that live there with their families but cant pull the trigger on buying a rental there. 

You’ll most likely have many conversations before you pull the trigger on your first deal.

Reappraise After rehab should allow me to pull most cash back out of deal.

May be a great way to build more equity in it if it costs $25K to finish but would be worth $375K once done and rented.I think the house hack is a brilliant idea and depending on where this property is located should easily pull in $1200/month per unit. 

Might help you pull he trigger quicker when you are starting to make offers.

In 6 months we will be able to pull out a HELOC and recycle the cash to purchase the next one. 

Any suggestions to pull this off successfully.