Originally Posted by
FBinNY
As Andrew noted, the secret is peddling faster vs pushing harder.
That said, 49/14 is not a very high high. Most road bikes today top out with a 53/11 or 12, so your ideas aren't unreasonable.
.
Most road cyclists don't shift into a 53/11 or 53/12 until they're going at least 33 mph.
Chain skipping is not normal, period. It indicates bad rear derailleur adjustment or alignment, a worn chain, a worn rear cluster, a worn chainring, a chain that's too long, or any combination of the preceeding. I suggest you do some research on what needs fixing before fiddling around with your gear ratios.