Therefore, I would not be putting myself in a position where I'm risking my personal financing and the potential go bankrupt.

Personal guarantees are a given as LLC's can be bankrupted easily.

But, the last guy updated everything and it bankrupted him...

If that is all a landlord considerers every time there is a issue they will go bankrupt.

Mostly because I disagree with the entire higher education cost, loan-till-you-die, can never bankrupt, no underwriting necessary philosophy that our government uses to give itself its #1 asset on its balance sheet.

Another example is Hernando County, where Brooksville and Weeki Wachi have a bunch of developers that go bankrupt and land is not bid on since it's not worth the starting bid.

Your LLC goes bankrupt, you lose your 100K property.

Without those systems they would go bankrupt or have a really hard time running it smoothly.

Only have $1,000,000 in liability, well you have your insurance pay $1,000,000 and you bankrupt the LLC to pay the rest of the claim, but of course that means you lose everything inside the LLC.  

NYC co-ops are a great way to get more than a closet sized apartment without going bankrupt, but they are definitely seen FAR more in the City than any of the suburbs, but I, personally, am pretty anti-co-op, especially for investors.