BiggerPockets is a great way to network to find these people and ask for recommendations of those that serve in your area.

Medium grade sounds much better when you walk on it, your installer will not hate you and is also more resistent.Any certain brands of lvp you recommend?

North-east Charlotte and The Triad area.Would you recommend any knowledgeable builders and GCs who have experience in multi-family new construction?

I would recommend housing hacking however I'm assuming you are pretty comfortable in your current home given where you are in life.

I would take any recommendations you have for property management as well.

Dillman (Author)Also, I've tried searching for a SIOR reading list, and found these three titles:Confessions of a Commercial Real Estate BrokerThe CFO's Guide to Understanding Corporate Real Estate TransactionsGo For Broker: An Executive's Guide to Hiring a Broker for Today's Complex Real Estate DealsAre there any other books you would highly recommend? 

Metal roofs are highly recommended and should last for a long time I'd want everything to be gone form the old roofing and everything inspected properly before the job gets started.

I’m very close to entering the STR market and I may very well be taking a major risk and loss being too late to game but i did decide to do what you recommended (before seeing this post).

I'd recommend checking out some turnkey property managers to get a sense of the numbers. 

Any softwares you would recommend?