Thanks for the good advice, especially #2, I need to start seriously working on the income/savings side. There's food on the table for the family, but need to save more for these 15 years for sure...

I looked into doing an MS, but I already have one (obviously not in CS) and with all the information and tools freely available now...I am leaning towards building stuff and using it as leverage for #4.

I am after the skills more than after the degree, I can move much faster that way. If a field really needs the degree I will try another one, this strategy worked with web development, so I will try that first and see.