He makes over $230k annually. 

I am about to submit to the IRS my log of 500+ hours working in the STR business, most of which come from communicating with guests, cleaners, maintenance people, Airbnb, VRBO, and managing supplies, shopping, bill paying, pricing, calendars, all the daily and weekly tasks. 

It has a slightly more vacation-friendly vibe with its arts scene, annual events, and outdoor activities that draw visitors regularly.Since you're targeting STR occupancy over 50% without extreme seasonal dips, you might consider neighborhoods near popular attractions, like Tulsa’s Downtown Arts District or the lake areas nearby, which offer steady, diverse visitor interest.

If you spend it on unpaid rent or maintenance along the way, you'll deplete your leverage.2.

Ask the manager to explain their process for dealing with maintenance, late rent, evictions, turnover, etc.

I am a retired RE Broker with decades in the business and thinking of returning to it as either a Wholesaler or a Fix and Flipper, areas I have completed before and have experience in, and, having performed a lot of due diligence, I once again have been confronted by con men saying they are not gurus then try to sell me a service at $97 per month, or $129 p/m ( billed annually, with no trial period and no refund which comes out to being charged (1,548.00 ) along with other shysters charging upwards of $20,000 for a level in which I could actually MEET the Guru and bow before him in abject humility and profess my undying devotion to him for his enlightenment, while making my wallet lighter and my stress greater.

Your cashflow is decent for the two investment condos and you have reduced maintenance there because of the HOA (but you have HOA which is a hindrance), but I would rather sell those and trade up to a multi with no HOA.

@Chris GrenzigYes, the long term tenant’s unit would require a lot of work to turnover. i met him and he seems to be nice and low maintenance so I’d like to keep him in place. 

The cash flow you earn from rentals will likely be best spent on maintenance, unexpected expenses, and reinvesting in future opportunities.

@Devin Voelker$1,800 x 8 months occupancy = $14,400 annually $1,200 x 12 months occupancy = $14,400 annually Are you confident you can get over 8 months occupancy for the midterm?