I'm eager to grow my book of business in various markets and connect with active wholesalers.

Feel free to inquire about their staff qualifications if it's a larger organization.2.

I wouldn't feel good about convincing someone elderly to sell to me and then turn around and wholesale it. 

You might check with your Self-Directed IRA Trust Company/Custodian, they might have a brokerage connection capability where you can setup a brokerage account tied to your IRA, then you can with that brokerage to invest in various public market investments, in some cases stocks, mutual funds, ETF's, treasuries, and CD's.

Quote from @Shiloh Lundahl: @Jay Hinrichs so it sounds like you don't feel like you got punched in the face by real estate over the past couple of years. 

The $300 cashflow is a gross number though - you will invariably have expenses that will eat into this number.

Thus, I started looking into vacation rental and co-living platforms to see if I could get the same level of comfort building a portfolio of properties in various cities.

Any advice on how to get out of this stagnant stuck feeling?

I have dabbled in various types of real estate investments, ranging from small multi-unit properties to single-family homes and commercial buildings.

It was an ongoing issue that ultimately resulted in various sets of tenants yelling at each other in the middle of the night.