Real Estate is a competitive game, and Internet and BP have leveled the playing field for anyone who wants to take advantage. 

I would always contact a CPA in this field. 

That said, I figured that I might get some good feedback from all of you to save me some trouble or at least help me narrow down the field!

Anybody experienced in both fields that could give some direction?

They will certainly give you a professional view of the field and guide you through your early process.Best wishes to you on the journey!

Can't thank you enough for the specifics and being in the digital field, I truly appreciate the digital tactics.

Of course these properties are old, and require more maintenance than others somewhere else would.What I'm getting at is that my skill set, my area, and my mindset regarding investing complement each other in what I've chosen to do within the field of real estate investing.

We selected an area that had good summer rentals (obviously because it is a lake house), but we also found a lake near a very good football program so we could also get fall rentals. 

It is better to create a system to narrow the field of properties, and then run the math on the ones that fall into the narrowed criteria.

And your career field is a huge plus, as well.