On the 4plex I would recommend having it inspected to see if the systems are in good shape, and getting some contractor quotes on what repairs are necessary to make it safe and functional.

Once you have a short list, get an account with each one and run them through the wringer to see how they really function.

And that's not even mentioning how disruptive and disrespectful some STR guests have become, nor the constantly evolving and restrictive rules imposed by the STR platform, nor the fact that we're at a market maximum in terms of valuation, nor the fact that I don't plan to stay in California much longer.With all that said, if I was a whale planning to stay in California I'd spend the money to fix it up, combine the 2 top floor units to make it a 2/2 master suite, reinforce the roof structure and add easier access from inside because the flat roof has a 180 degree panoramic view of downtown from the Coronado Bridge to Balboa Park. 

Hard money loans are more appropriate if the property is not livable (with conforming loans the house has to functional, although still a mess), or you are a more seasoned investor and it fits in your business plan.Hope that helps. 

Does anyone have thoughts on how to make property management companies functional for us owners?

The idea of combining digital marketing into real estate and contracting is still just an idea.

Currently, have OLM which does not have the function (yet), and another database that only allows to campaign to one property owner.

They typically will not look under the floor boards or in attics or dig too far into mechanical stuff as long as the systems are functioning. 

and I got very familiar with my PV function on my RE calculator until you run the PV you would be surprised .for instance a 30 month Zero interest fully amortized note has he same cash value day one as a 15% 7 year note.. so in the day were we did land sales with seller carry back and our note version of BRRRR  we always looked at what our note buyers wanted for a return then manipulated the terms to meet the note buyers goals..   

Combined rental income would be approximately 36-40k per year)