Here's where I'm completely stuck....I love the idea of finding a small "farm area" and learning it inside and out, the problem is, I use the term Greater Rochester Area in a broad sense, and it's huge. 

(I know that broad question) I know of rent manager and quick books, but is there any other software or apps that I can use?

That's where you're going to find your largest selection of properties to potentially buy and your largest pool of buyers to resell to.The thing about flipping in the lower end of the spectrum is that it's WAAAAY too easy to over-improve the property.

Broadly speaking, 6 months of inventory (meaning if no new homes came on the market, it would take 6 months to sell through the supply) is considered a balanced market. 

You asked a pretty broad question, but if you're still interested in learning more about marketing via Facebook, I'd be happy to help, either on this post (or another one) or by DM

Trust me I have a friends on both sides of the spectrum and happiness lies within yourself and not how many doors you have.1) What is your money passive income number you want?

Painting with a very broad brush (as going into every community and intricacy of Hilton Head on this platform would be too long of a message) a few suggestions would be as follows: MTRs - If this is your niche in real estate - you honestly may have more success in Bluffton for MTRs.

@John AndrewsHere in the Bay Area, I have success with both ends of the spectrum.

I "feel" like given the fact that not a lot of 3 bed 3 bath properties exist in the area I can land near the higher end of the price spectrum as an LTR, $2200-$2500. 

How much is up to the amount of work you put in.You stated 2-4 units in Newark, which is very broad and almost 60% (good guess) of its inventory.