I am not sure what the availability of cleaners in that area so I would spend time right now see what is there before committing to a property.Also, if you are spending 2k a year on fixing or replacing stuff, you are getting the wrong guests.

However, we just started STR property management and it would be very helpful/look more professional to have the ability to esign contracts, autogenerate payout statements, direct deposit payouts, ect.  

Quote from @Alex Yang: Professional remodeler, first time builder. 

Next property will find a professional Realtor who is experienced with marketing their listings and closing deals.

Ideally, meeting with clients at least once to twice a year if their situation warrants it, especially if they have real estate professional or STR loophole. 

I can see an explicit exception in CA Tax Code § 17561 that says you can not use the qualifications in Section 469(c)(7) (Real estate professional) to render that income as non-passive, but I see no callout for 1.469-1T and, as such - as a non-CPA - I do not (yet) see a reason why we cannot follow the same rules for CA that we do for our federal taxes; e.g., if the business is not a "rental" business per tax code, we count that income as non-passive and offset other income (W2, etc) similarly.Does anybody else have some guidance (or opinions) on this matter?

They want to pick up the phone and call or text and get an instant response from their cleaners.

I’m a professional civil engineer with years of experience in construction and entrepreneurship.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

For example, my cleaner and handyman at my STR have separate cards so the only thing that ever gets charged to that card is that expense.