Spend more than half of your total working hours in an RE business in which you materially participate.2.

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

Unless you have $5 - 10k MONTHLY to spend on marketing this is what you need to do to have any chance for success with wholesaling.  

Spending $15,000 on minor updates in a Hyde Park two-flat could raise the rental unit's value by $300/month.5.

I’ve got great tenants in my SFH so I spend very little time on that every month but in my market the Multis just make more sense.

If you or your spouse materially participate in the property by spending at least 100 hours per year actively managing your STR and more than any other person or business entity, and the average customer stay is 7 days or less, the answer is yes.

The warm months are now approaching but, for the future, I'd suggest coming in aggressively low during winter months and looking for an 18 month lease to start - that way you'll renew in a better pricing period and see some income while you wait rather than spending three months with none.

Like you I also have the RE license to keep some of the commissions and better control. 

You’ll develop resilience, leadership, negotiation skills, vision, emotional control, and more.

It sound like you have your area under control.