No matter how good your systems are you will likely end up in that city a few times per year at least, especially in the early years.With that being said, once you have your core team established in long-distance investing, it becomes much easier and problems equal google searches for vendors, phone calls and book keeping in your life (project management) vs. swinging the hammer or fixing a toilet yourself because you're forced to put those systems in place.I live in a similarly expensive city and would honestly be stoked to find a duplex in Denver for $600K!

For extra insurance, you may want to start giving 10% of your bookings to another cleaner to establish a relationship in case anything happens with the 1st cleaner. 

If you're established enough as an investor that you're already doing projects and own assets, it's highly likely that taking the time to save 10 cents per letter by doing it yourself is not worth your time.

Is there any benefit to establishing a “parent” LLC that would own the separate property LLCs?

Although, I think it would drive up the cleaning fees and, in turn, the airbnb rates to have cleaning/PM companies that establish and maintain a higher standard of work.

Does anyone have any recommendations for how to collect monthly rent payments digitally into an established account?

Furthermore, establishing a solid network within the real estate industry might offer beneficial insights and potential deals.Feel free to share more details about your specific market, goals, and constraints, and the community can provide more tailored advice.

While I'm not saying an MBA  is required for real estate the benefit to our business is focusing on establishing systems & processes to run our business along with metrics to monitor how we are doing. 

Would love to join, if my offer is accepted I will suddenly have 2 STRs because I spent the last year converting and living in a 35 ft school bus that I plan to list as a unique STR, while I house hack the new property(The property I put an offer on has an established AirBnB). 

I established a  mgt entity for leases, deposits, income, expenses, but never held any of my dozens of residential rentals in LLCs over my 21 year run.It's just tougher to get good mortgages and insurance.