Really? In all my dealings over the years with H1Bs, you're the first person I've ever met who was blase about ignoring immigration law.

Wow, what a Mad Lad!

While it's true that people rarely get forcefully deported for overstaying visa, how is being in the country illegally going to be an option for a programmer? The whole 60 days "grace period" is about transferring visa without leaving the country, other laws still apply. E.g. INA 212(a)(9)(B), which makes one inadmissible for 3 and 10 years after 180 days and and 1 year of being out of status. Since H1B "transfer" is actually a new visa (that's why, in general, you'd have to leave the country, get a new visa stamped and return in a new status but USCIS kindly shortcuts it for people who are just switching jobs), you will be automatically denied it as soon as you have accumulated 180 days out of status and became inadmissible. What's next? Nobody is deporting you, sure, but how do you live? You cannot work legally. You cannot re-enter country if you leave. You probably do not have skills to work jobs usually done by illegals. What do you do?