One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

Connect with other investors, agents, and property managers to get a feel for the area and learn from their experiences.Are you thinking about house hacking or just straight-up rentals for now?

Our lot is fenced in and we cannot see where he lives but close enough to be of concern, but we want to stay in the same town until the kids are finished school.So, my question is this, would it make sense to rent our home (roughly $2300-2500/mo. as per real-estate agent claims), with the stipulation that the garage is used for my business AND buy a home nearby?

You will need to vet out a few agents or you can work with reputable wholesalers.

He seemed like a big-time agent who works with a lot of long-term investors.

No agents involved.

I do have a third goal, but too much will happen by the time my second goal materializes that my third goal will likely change drastically.Also, I tend to find myself wanting to ask market-specific questions to agents/lenders/investors/contractors/etc. a lot.

For on the ground evaluations, I rely on local contacts: agents, contractors, or even property inspectors to provide walkthrough videos and detailed feedback.

All our data was well-organized and cleanly presented (no dropping off boxes of unorganized documents in their lap).  

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?