One couple wants to earn money to put their kids - ages about 12 to 15 - through college.

The owner is old school and will want his payday all at once, but I assume after trying to sell over ten years ago and their advanced age, there has got to be so pain somewhere in there.

Since I do the roofing myself, it would be less for me to replace the roof myself than to submit a claim due the ages of the roofs (most are 9+ years).

I realized a couple of years ago that even at the age of 32, I did not want to be stuck in the rat race for the rest of my life.  

I am the father of two 3 year old twins girls and two sons of the age, 14, and 13.  

Age of homes?

That's a wise age...I think :)

I just became aware of a situation where a family friend and her mother have offered to short sale their home with no regard to loss of their initial $20K down payment and damage on their credit due to the fact that they're up in age (one is over 100 years old) and they see no other recourse.How can I advise them of a different strategy to resist the temptation to give away what is essentially a really nice home that needs minimal TLC in the Oviedo FL area?

I started working (at age 14) for my best friend's dad. 

Frankly, that's not how I'd build a list, however if that what you're going to use, then start by ranking your 45 properties by owner's equity, length of ownership and age of owner.