This will help you with the money aspect.

I think the most overlooked aspect is keeping the house as an original single family residence, instead of converting into a duplex.

Well........they sent a picture of a section of the roof, some of the shingles are u and guess what- NO insurance on it now.    

One of the critical aspects of successful property management is tenant screening.  

I have a strong work ethic and don't shy away from hard physical labor thanks to my granddad making me carry pack of shingles up on roofs at 6am during my summer when I was 11 years old, my pay was dinner that night lol. 

I'd also like to work as a contractor to work with electricians and electrical contractors as that would be relevant to my skill set in the engineering aspect.

I am looking to cash out, so i would like to know if i should be adding more money into the rentals such as painting/roof upgrades?

This stunning home boasts New hurricane impact windows, Newer Water Heater, A/C- 2020, and Roof -2017.

If you replace them now, then hopefully less headaches going forward.For example, I had to replace a roof on one of my duplexes, so I asked the roofer for a combo deal on another duplex with an old roof to get a better deal.

That is why crime is an important aspect of this.