I also probably wasn't as educated as I should have made myself, so I'm sure there were decisions that could have been handled better.Part of the reason I wasn't willing to deal with the hassles was because I had 3 young kids. 

Her reasoning is that she put it in her schedule and she could have accepted other cleaning jobs. 

Seems reasonable to me.

I like umbrella because there is no worry of being pierced for inadequate separation of finances, if sued you have a heavy weight in your corner who has all the consequences of a defeat, and because usually it is reasonably priced (mine today is not so reasonably priced but I believe it is mostly related to the risks of CA).I do understand that the probability of needing the umbrella policy is low.  

The reason is the rent-to-price ratio is good so you can cash flow, and most of the West side doesn’t have a Point of sale inspection which is really annoying.

Quote from @Elinore Aguilar: The best way is to have the best firm with a reasonable rate and trust reviews.

This is one of the reasons I use a CPA for everything.

I am hoping to find a reasonably priced photographer to take some sharp  photos of a Property. 

What is the reason?  

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.