I totally get your point and I agree with you, that outsourcing the daily landlording tasks will allow me to work "on" rather than "in" my business.  

@Joe KimA few things to keep in mind about bookkeeping/outsourcing.- Get to know your bookkeeper before you make a decision on who to go with.

Also, did you do the cards yourself or outsource them?

I know that I can just outsource to a broker but A) that defeats the point if someone else actually ends up managing it - he doesn't want that and B) I'm not charging him enough to cover outsourcing.

Basically Outsource it.

As a firm, being licensed in key states is important to sustainability of business and in some cases we outsource loans in states we can't touch.

There have been a few headaches recently, and I am considering outsourcing the management to a property management company, or some alternative option that will remove me from day to day management.

You can write it in the lease it is up to them to maintain the lawn, otherwise, just outsource it to a company

But not before burning thru millions of venture capital and screwing hundreds of businesses falling victim to their sales pitch. https://www.forbes.com/sites/davidjeans/2020/07/20/scalefactor-raised-100-million-in-a-year-then-blamed-covid-19-for-its-demise-employees-say-it-had-much-bigger-problems/Some points worth highlighting:- "Instead of software producing financial statements, dozens of accountants did most of it manually from ScaleFactor’s Austin headquarters or from an outsourcing office in the Philippines"- "Some customers say they received books filled with errors, and were forced to re-hire accountants, or clean up the mess themselves"- The annual  contracts mentioned in the article were $23,000 for an e-commerce business and $6,000 (and triple that amount at renewal) for a coffee shop.

Makes a solid case to outsource your property management in my opinion.