@Sean October - keep in mind that from Fort Pierce to the border of Brevard is at least an hour drive.

Any recommendations based on your own experiences with cross year projects and tax filing? 

I know some of these would be cross benefits of the others.

We also buy our properties distressed, so we have some aspects of flipping in that we have to either do the repairs or oversee them depending on the project but again that's about the end of where our path and the flippers path crosses, I have flipped a few properties but I am not a flipper.I spent the first couple of years as an RE agent, because I thought it would be a great stepping stone into the business, I was a good agent but never a great one. 

@Janelle Hicks -- if they're all around 12 months of income each, you should be able to do a portfolio loan (or a cross-collateralized loan) with a non-bank lender (aka a HML or DSCR lender).

I would begin with a cross-reference of the parcel in the legal discretion with property tax records to verify, then go from there in the assumption of proceeding with it as the purchase of one property (singular looking on paper, plural in real life as it's been built up).I would also be curious (just based on the SqFt you mentioned) what the assessed building value was- if it were based on (what I would assume was the original dwelling as the rental) and if the new 10,000SqFt building was an addition not yet assessed)- only mention as if it's not that's a hefty improvement to think of paying taxes on (at least in most areas it would be)It seems like your most inexpensive loan product would be a conventional mortgage then, if it does indeed adhere to being 'one property' on paper. 

I just recently bought "Rental Property Investing" - by Brandon Turner and it is my second day reading so far and I have come a cross lots of information which have brewed up many questions.I will start with some of the main ones I have and if anyone has an insight I'd really appreciate the help.

The land is directly bordering National grid power lines as well as a fenced in national grid location so it seems easy for the company to tap into the power lines.

You know in movies when someone is shipwrecked and crossing a desert and they see an oasis on the horizon but they aren’t really sure if its real?

It sounds like you are getting areas crossed and these Cleveland neighborhoods are EXTREMELY different.