North Carolina Newbie - Seeking Advice

[Charles Murray]

Hi all! New to both BP and RE. I'm from Raleigh, NC and am currently in self-education mode (lots of books, podcasts, and mentor seeking), but planning to explore my first deal soon. 

I have a full-time job with a marketing technology company in the area, but have a strong interest in pursuing RE investing as a future additional stream of income. Freedom is the real reason I seek true financial independence, and I'm willing to work for it. 

I plan to start with a single-family buy-and-hold rental. My goal is to own five cash-flowing properties in the next five years. I then want to expand to multi-family and potentially commercial investments, scaling from there. 

I'm looking for advice on analyzing my first deal. 

How does one accurately estimate expenses to ensure positive cash flow? Are expenses primarily estimated from gathering info from the seller combined with my personal discoveries of the property? Is there a comprehensive list of expenses to consider to ensure I don't miss anything (taxes, insurance, fixes, etc...) when calculating rent to charge? 

Open to any/all guidance here. Thanks in advance!