I work a 9-5, am married, and have 2 kids under 3 years old so I don't have a ton of extra time to actively find, fix, and flip properties.

This is the best answer, and is the basic spirit of what business people have to consider for all of their subcontracting decisions.

I’m married with kids and own a primary residence, so no house hacking for me!

., very basic question. 

Knowledge is power and for me, it builds my self-confidence so I’ve been bingeing podcasts, books and also recently gotten my real estate license so that I could have a better understanding of real estate in and of itself, with the hope of building upon that basic knowledge with what I’ve been learning about in real estate investing.

So basically I'm at risk of the tenant damaging my property and not having a way of going after her because she is not signed to the lease. 

We are now considering house hacking by buying a neighbor’s house due to our kids' school proximity.Our monthly expenses for our current home are $3,000, and the estimated rental value is $2,300-$2,350.

Basically do the work above and beyond what the average flipper is doing and you will find/get the deals before they do.  

It sounds like you have the basic 20/25yr 3tab shingles, which yes are prone to "flip up" or break off, esp as they get older.Find another local Roofer, that for sure taunts that they do Repairs, will warranty their work, and get the repairs done. 

Basically only NE Jackson has owner occ activity Sojac very little to none anymore all investors who are only going to pay for what ever the cash flow is and deduct for risk.