Is that enough spread to be comfortable? 

Assess if you have enough time for tasks like tenant screening and maintenance.Expertise: Professional managers know landlord-tenant laws and property maintenance best practices.Cost vs. benefit: Weigh management fees against potential savings and efficiencies professionals might offer.Property location: Distance from your home to the property matters.Number of units: More properties increase management complexity.Stress tolerance: Consider your comfort level with tenant interactions and problem-solving.Long-term goals: Professional management can free you to focus on expanding your real estate portfolio.

I've not invested in CA, and I'd enter that market extremely cautionsly based on various rent control issues, eviction issues, and the political environment seems to be very unforgiving for landlords. 

I feel like renting out multifamily is what I may be looking for with this, if done right can give me cash flow, I can hire a property manager at some point and I am friends with a lot of home improvement companies, and I could either use some money I have saved up to put a down payment or home equity loan for some % I am comfortable with and pay both off as fast as I can and repeat.

I would recommend only using a short or mid-term rental house hack for a 2-4 unit property or a house with a detached ADU for your security and the comfort of the guests, which will make it more profitable.

I did a similar thing, instead of a GC, I was an engineer  already in the land development environment and put together my own group to purchase land, entitle, develop, etc. 

Some people are not comfortable with older product.  

.- I've been on the sidelines with this weird high interest rate and volatile environment for about two years now.

This would make lenders more comfortable lending to you, but it may be a harder sell for the family member versus just a promissory note.3.

I love that you rented two of your bedrooms as mid term and short term rentals and made enough to pay for the mortgage and now you are going to use the rental income to show you can qualify for another property.This is an excellent strategy and one more people should consider doing in this inflationary environment to offset the biggest cost in their budget--housing.As you rightly point out, you can use this strategy with every house you buy accumulating a portfolio of houses that you originally started out living in as a primary residence every two years.Well done and more people should consider doing the same, or rent their garage, or shed, or a boat, or an extra car.Love it!