I plan to ask the seller a lot of questions to find out more details about his family's situation....but fundamentally, what rule of thumb do other investors use when negotiating an off-market deal?

Start with the market, pick one with good fundamentals, then find a broker or turn-key property management company on BP, ask them questions, and build rapport with them.

Which brings me to my topic, how do I know if I have a solid analysis or not because I have been doing on average 1 analysis per day for the past about 2 and a half months and I haven't found even 1 deal that cash flows, its always around $100 or more in the negative.So my fundamental question is how do I know if I am just being way too conservative with my analysis or does that sound normal with the amount of bad deals for 2 and a half months straight?

Ohio is great for cash flow and appreciation hybrid, specifically Columbus has great fundamentals and numbers and I’ve enjoyed growing my portfolio here.

Having a good understanding of these items will tell you whether you are just having a temporary rough start or if there is something fundamentally wrong with your purchases.

You may 1031-exchange assets, postponing your capital gains and depreciation recapture indefinitely or even eliminate them permanently if you never sell and leave the wealth to your heirsBesides the benefit of being a passive investor and utilizing other people's experience, one fundamental advantage of syndications is an opportunity to invest in larger assets that an individual or a small group simply cannot afford.

I sparked interest in real estate investment just recently and I am very excited to learn the basic fundamentals and with due time begin to get my feet wet! 

I would argue that graduate school and undergrad are fundamentally different.  

Originally posted by @Ken Weiner:Yes I am using accounts of type Business Fundamentals Checking from Bank of America.  

Look for track record, conservative underwriting, a good team, good market fundamentals, and a solid exit plan that provides you with a 1031 escape hatch.