If you waited around for years between inspections In a c or d class neighborhood you’d likely be in for a rude awakening when you opened the door to your place only to find it has been converted into a crack house with graffiti on the wall and a basement with two foot of standing water in it .

If you go in with guns blazing with all sorts of demands and treat the seller with suspicion, you're setting negotiations off on the wrong foot. 

Should I wait to graduate and simply start off by house-hacking a few triplexes/quads and go from there, or should I start actively looking for deals to utilize my private lender and to get my foot in the door and start scaling as early as possible?

Does anyone know of a rough estimate per square foot for complete rehab costs in the Hampton Roads area?

But the first time he approached me on foot.

In that instance you'll find that most national QIs with a large foot print can and will take the time to spend to make you and your client comfortable.  1031 is a federal statute so acts the same way and is structured the same in all 50 states. 

How much insurance coverage do you have and does your policy even cover a dog large enough to jump a six foot fence?

As long as you have the right team in place, there is no reason for you to ever even step foot in the property.

Assuming going rates are NNN $1/sq foot for restaurant space, what is a fair price for the  attached patio space?

Best advice on here is to keep stepping foot into group conversations and meeting people, rather than just the lone wolf studying.