Currently, we have a commercial policy with State Farm but when our lawyer reviewed it, she recommended we increase our medical liability coverage.

In fact, you'll learn valuable skills about managing rentals that most landlords don't learn for decades.

I spent the last 25+ years of my life in technical and executive recruiting, and now looking to taking some of those hard-earned skills and applying them to the world of property wholesaling/investing.

They know what they are doing and price the job accordingly.Over time, you'll meet a general contractor and/or a handyman who you like and can help out as an individual, but in general I just use the skill-specific established companies. 

We are able to do short term rentals with the other unit and learn many skills throughout the process. 

Just like everything else in life, get started, keep honing those skills (i.e. keep reading, keep learning, keep attending the meetups) and watch yourself get better and better witch each property you buy.I hope this helps and good luck on your real estate journey!

That is like getting in a plane versus a car and the pilot is like “I am new to this”… Curious and do not want to sound mean - but what qualifies you to have the skill set to buy this type of asset ?

Some training or skills should be required of the animals to get this certification.

If you are already good at finding and tracing deals and owners, use that skill to leverage with other investors who want more deals.

It sounds like you already have the skills for deal flow since you've wholesaled some properties and you'll have the cash savings built up.