Becoming a property owner.The hardest part about this right now is underwriting deals, remaining patient and disciplined.Outside of that, the actual details of managing the property are only hard if you do not have systems in place, delegate responsibility, and don't fully comprehend what physical asset investments require-- capex & opex heavy.

I certainly want to err on the side of caution in terms of investing in a pricier asset (at least in my RE experience thus far). 

Forming a business to protect my assets is an area I need to gain more knowledge in.

Occasionally if they have other assets maybe she can keep the equity of the house and he gets to keep his full 401k or something like that.   

There will also be many homeowners who have had the properties in the family through generations and own free and clear but now still need to obtain a construction loan to rebuild. 

If you can rent 3 units for $2,000 you are close to breakeven.On the plus side, you will have a highly attractive asset and several decades without much cost of capex and repairs. 

While they were good about obtaining a refund, etc., it still took time (and all communication is via chat or email, for me, chat was easier).

Yes I definitely need to obtain a network of brokers locally here in the commercial/multi space.

Account Closed said, income and assets are the only "hassle" with a conventional loan.

Sounds like it is best to either use the HELOC or obtain a conventional mortgage rather than using a HELOC and then a cash out refi.