Bought the house in '08 and when the seller bankrupted a couple years later, they lost the house.

Do they call you and say "Hey, sorry about your luck, we're going bankrupt.

SFH are extremely difficult to cash flow and a vacancy can and does bankrupt many investors.

If somebody just went bankrupt, A) They have a history of doing that, and B) Their credit already sucks so why not do it again?

I don't know when they'll go bankrupt, but I'll be a 'paying' customer until then.

If an HOA gets enough people who don't pay it can bankrupt them. 

In turn, that means that buying this home is going to bankrupt his business!

I have been in different professions that I have chosen (home loans, insurance, customer service, sales, and plumbing sales) all in some way related to my end goal of educating me leading to being financially free through rental properties but I have never made the jump to action partially because my funds are low and credit got killed by an insurance company that I was working at which bankrupt and closed the company without paying me 85k. 

Certain tasks need to be performed especially in your due diligence and acquisitions.Learning the basics of real estate should open your eyes to  the socio-economic factors of real estate, especially residential, understanding you market, location, zoning, adding value which all ties into marketing to meet socio-economic demands.Most assume someone will want the house, that can bankrupt you.

If you're in the position to put down large amounts of cash that means you have it, so unless you're keeping it under the mattress you'll need to do something with it, either invest it in the things you're most interested in - real estate or diversify it into something else - stocks... etc...Cash is king for a reason, when we use cash we get deals that we would miss, cash give you power over your competitors in a competitive market or a very desirable property, it allows you to often get better prices (lower) on properties because sellers look at you as being guaranteed to close versus those with financing contingencies.For everybody who talks about leveraging, there were 20 who went bankrupt in the last recession who were leveraged and believed everything would just continue to go up.