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.

Do a search on any of the SaaS solutions or apps out there to deepen an educated decision.I have tried quite a few lead gen apps and other workarounds in the past, most are not helpful.

There's a reason for that.While I think taking 300k in loans should be avoided at all cost, I don't think investing to band-aid that problem is a viable solution.

On top of this, you need to be able to determine if a property is a good deal, and you then need to pull the trigger immediately or someone else will grab it.