Do your best to keep your Profit and Loss calculations pure and then manipulate those figures however you choose in order to figure your personal analysis.Note that some accounting packages will create a Statement of Cash Flows for you. 

This assumes a pure cash investment. 

Would you say taking into account my market's trends when it comes to rising rents, property values, and moving trends is pure speculation or a legitimate investment analysis?

Purely from an investing standpoint, I love the little cabins the best.  

I got my license purely for the buy/list purpose of my investment properties.

If in or around Boston, could be owner occupied for different financing if needed, if in Florida, pure investment and would also need property management company to own the process.New to the process, love the interest and help from everyone.

Sounds like you are doing all the work and they are purely financially invested.  

The Chicago market is not a pure "cash flow" market, so there is a lot of appreciation potential as well. 

I'm as well a NY State licensed Real Estate Salesperson and do it on the side purely to learn more about the RE market and help in my investing. 

The budget I was given was purely for the conversion, putting a map on the property as well as fees from the county.Thanks,