I just wanted to get a sense of what I could be in for if the opportunity to move forward actually materializes.

I actually have a friend who moved out of his first house (that still currently has a mortgage backed by a VA Loan), and was able to use the VA Loan for a 2nd time to built out another house.

This would actually be my third deal.

If you have a nice team, maybe your management company won't destroy your cash flow with a million needless expenses that you have no way to verify to see whether they are actually necessary.Just a heads up from personal experience in living in the Akron "war zone," I would never invest out of state in Akron without local assistance.

As others have said, YMMV depending on what it actually currently looks like and your market, but for me renovated kitchens help sell rentals that are otherwise "idiosyncratic"  walkups with very small bedrooms, slanted floors, uneven walls or sometimes all of the above.

If this were done it becomes very obvious how equity kills a properties actual cash flow.

My dream scenario would be to meet other investors that I can just talk to in order to bounce ideas and numbers off and have actual discourse. 

The answer is likely two-sided: 1) Your income and financial situation determines how much you can actually afford to spend on housing, and 2) You find housing that fits your needs and shop around for the best deal. 

Also, if you don't find the right meetup for investors with what you're looking for that would actually be a huge advantage because it gives you the chance to start the meetup.

Do you have any actual experience with this?