Selling it now vs renting, will give your dad more money and he won't have to worry about renters or cap gains. 

Note: We do 50+ investment property loans a month and the most important thing I tell BUYERS of properties being sold as or soon to be STR is make sure you are paying the market price per square foot and do NOT buy based on income approach/CAP rate.

Short term it is difficult to make the numbers work, the cost of new construction and the time it takes to zone-plan-build are usually the main reasons why private investors stay clear.

, but very difficult to DIY remote manage.

The plan is to use the heloc to purchase additional properties, and basically brrrr and pay back the balance - then repeat.What I didn't realize is how difficult it is to find a business heloc.  

The agents are charged for this service no matter what so it's difficult for the agent to service from a time and financial perspective.

Very difficult to be successful with this program when buying in these lower tier markets unless you are hands on as you say and yes, scale is necessary to achieve efficiencies.

Really difficult right now.  

These are difficult decisions.

They are very difficult and expensive to move.