I hope this encourages readers.

I’ve found being in a mastermind of like minded individuals helps me excel more as everyone in the group encourages and wants me to succeed. 

In addition to encouraging you to join TRIG I’d encourage you to also check out the Hampton Roads Landlord Assoc and Rent Ready Norfolk.  

That's not my market, but it seems like excellent news to me - regulations like that encourage responsible ownership/management without severely handicapping the industry, and in my opinion creates a safer environment in which to operate a business without fearing that super-strict regulations could swoop in at any moment.  

Thanks in advance for any responses and/or encouragement!

Would anyone encourage or discourage me from doing this to start out?

To find one (aside from word of mouth), search for your state/areas society for professional engineers.

Now think about those companies who send you junk mail encouraging you to refinance -- they were probably at like 90%+.

However, I hope and will encourage the seller to simply work with the buyer directly to find a simple solution.-- Jamie Rose

I would recommend both...They both encourage you to just get started after educating yourself properly aa well as surround yourself around a great A-Team!