After a year of being a member I'm finally stretching out into BiggerPockets community. Looking forward to where this leads and any connections that may develop.

Should I contact a property manager?

•I plan to put 20% down on this new property, which means I’ll be left with about $80,000 in cash after the purchase.Given this scenario, I’m trying to decide whether to pay cash for the second property or continue with the 20% down strategy .

I am currently a utility engineer making over 100k/ yr, should I consider pivoting into the developer or construction management space for experience?

I am out of state so he managed it all from start to finish.

Each has it's group of followers and you need to decide which way you learn best along with whether your goal is to become knowledgeable alone or to become knowledgeable and to actually buy properties.

If I decide to pursue my studies there to obtain a license, do you think my completed subjects would be credited toward obtaining the license?

Hire a sober house manager who has significant clean time.

That does seem to help but most self-managers just use the 2 OTA without a PMS. 

This is perfect being 2 doors down from where we live so we do not have to pay cleaners and property management.