Much of what he purchased is now worth anywhere in the 4 to 5x's what he originally paid for it range.

What is typcially the busiest day of the week and of the month for onsite large multifamily property manager.I'm guessing early in the month 2nd-3rd when rent checks are coming in or starting to deal with collections.Maybe Mondays to start dealing with weekend applications, tours, leases?

You should be getting more personal, not less personal.

We co-invested in a large SS facility in a tiny town in Texas (ever heard of Beeville) from a mom-and-pop seller that turned into a home run for our investors. 

Sure, having a personal mentor is awesome for getting targeted advice, but being part of a mastermind takes it up a notch.

While rental demand is going down, there continue to be more people purchasing properties for personal use in turn causing there to be an overall shortage of rental units available in season.

Quote from @Cindy Zhu: Get a large contractor bag.

Is it feasible to finance both properties simultaneously, or should I wait until next year to sell and purchase my personal home?

I would have a leg up in that I am a professional photographer, and that my rental would have a large fenced yard, playset,and a playroom. 3 rooms with 4-5 beds.I did reach out to property managers and it seems i was undervaluing its revenue as an LTR.

if you buy a property at market price in a good neighborhood - you will break even or lose money.and in general, if you're serious about this, i'd recommend going to your chosen market in person, probably multiple times, to set up your team.