I agree, having a comfortability with debt is unavoidable, I also feel that I could find more comfort with that debt due to its necessity for investing.

We were really hit by 2007-2008 and I couldn't hold down a job for a while so necessity made me look for different options to keep bread on the table.   2.)

Necessity.- organize your totes.

Or is it truly a necessity to start small and get a 4 or 6 unit under my belt to prove myself before moving up to bigger deals?

I am just starting out as a rental property investor and I was curious if anyone feels it’s beneficial and a necessity to join the Real Estate Investor’s Association in the area that you are looking to buy?

Because my rents are lower ($550 - $700), there isn't much money left over for basic necessities if their rent is more than 33% of their income. 

The house has a lot of potential and just needs a lot of non necessity work such as refurbishing floors and putting drywall in.

It has forced air heating but no cooling unit, is having a cooling unit a necessity?

Housing is also a necessity and I personally like cash flow rather than appreciation so I'm not too worried

Yes but you don't have to, you can do the math and see how renting or buying local affects the amount of money you have to invest and see if it is worth it, but I'd consider living with my child something of a necessity and worth the cost.