I just don't know what the best way to go about investing somewhere I'm not totally familiar with or have reliable/trusted connections?

Again, just want to be 100% I trust the numbers I'm running. 

I feel like you shouldn't let fear prevent you from trusting or getting to know someone new.

Would love any advice on people who have bought property through business trusts, forming an LLC vs The trust, or advise on him buying the property personally.

Once you have a good rep & portfolio of properties it will be easier to A-attract investors, B-ensure trust and earn full operating trust.

Do you already have a trusted handyman or group of skilled laborers? 

The hardest part is trusting that this new move for our kids will be beneficial in the long run and I echo what @Shawn Mcenteer was saying about NJ being a great place to invest, but a hard place to start investing.

Real estate is an industry built on good reputation and trust.

Just trust me on that!

And, as you demonstrate success and build trust, you can get better rates and loan terms.