It's just a matter of gaining the appropriate knowledge (for me, the biggest thing is knowing financing & how to use it best) and then actually DOING it, which most people never do.Now, I've gotten the real estate bug and can see all the possibilities (& how your home is actually a liability).  

We held the property for 7 years and had good equity when we sold it back to the original owner.What we did next was our biggest mistake.

The biggest thing they teach you in real estate school is how not to break the law :). 

My biggest hurdle would be when refinancing time comes.

In our area of SWFL (Naples), the 2 biggest determinants are roof age/type and flood zone.  

One of the biggest advantages of having your rental properties in a trust is that it protects them when you or your spouse (or partner) die. 

Just don't be upsold into buying their programs and packages.The biggest part of personal finance is DISCIPLINE!  

Title companies normally act as escrow agents making certain the money and property transfers both happen.Issues about the condition of the property are the biggest source of problems.

Now, I guess my biggest fear or what bothers me the most about these potential houses is that most of these core things have not been completely gutted and updated in near 100 years and the sellers are asking prices which don't make sense to me if I were to consider gutting the property to completely redo electrical and plumbing.

Biggest thing about becoming a better landlord in an HOS is knowing the rules yourself,including them in your screening process, and explaining the common broken rules to the tenant during move in process.