And let's say I drop 20k on a house that generates only $100 cash flow each month; it will probably be at least another 6 months to a year before I'm able to amass this amount again from working my day job.

I have not found anything yet but I do need to make sure that I calculating my deals correctly.My the numbers my calculations generated were horrible.

I appreciate any suggestions the BP community has regarding lead generation, individual connections, etc.  

It is also a great way to invest in another market when you live in one that does not generate a good enough ROI. 

The other question is how should I know whether or not I have over leverage my property and will possible generate negative cash flow?

Over the long term, I'd like to buy and hold to generate passive income but prior to doing so, I have to generate funds.

Cap rate.If I were buying I would not give any credence to it being a SFH because the base "home buyer" mentality simply will not exist and therefor not generate the higher prices emotional home buyers bring to a SFH..

If I can buy another property which generates cash flow way more than 4% of mortgage rates, then why I don't just buy it but pay off 4% of mortgage?

Deciding what I want to achieve: I want to learn a great deal more about real estate investing and continue to acquire rental property that will generate passive income, gaining financial independence, which will give me more freedom with my choice of day job in the future.  

Started generating Cashflow.