The 10 year return on expensive markets like CA, Seattle, Boston, etc. obliterate those of cheap midwest markets.

I'm hoping to branch out into additional investment properties but the $950/month that I'm seemingly throwing away makes this difficult.I thank you all in advance for your thoughts and feedback.

I would throw in a few more out there for you like Listing optimization: Rankbreeze and Intellihost, Data Companies: AirDNA, Mashvisor, etc., and guest verification platforms like Superhog or Chekin.

Nor cheap. 

Be aware that in many areas this process is neither cheap nor quick.

Throw in some extra costs like moving expenses, professional photos (a cost the STR PM may also need to pay depending on the quality of the existing photos), renter's and lessor's insurance and a listing on furnishedfinder to round out some of the start-up costs.

Part of the premise of hiring a manager is that they will manage repairs, including efficiency of repairs.Anyone can pick up a phone and throw unlimited amounts of money at a vague reported problem.

Then I bought another "cheap" $400 printer and although it was fast (70 pages per minute), the envelope feeder only held 8 envelopes at a time.  

Be wary of “cheap” STRs and 10% down “managed for you” deals especially in Orlando.  

It's so easy to have some magnetic signs hanging around to throw on your other vehicle if you want to go do a bid and not take your big ole truck.I have no answer as to why they don't take advantage of this.....it's just dumb (maybe there's your answer :-) I have the company name on 3 out of 4 work trucks .