I will be heading to Open Road in the next few days to get the last few items for my fixed/free conversion. I need to get a freewheel, cog, and chainring. I recall Roadfix recommends a 2 tooth difference between the freewheel and cog. How does 44/18 free 16 fixed sound for Pasadena area riding with the occasional 30-50 mile ride.

I will mostly be riding around town, around the Rose Bowl (likely not up steep streets in the hills around the Bowl), and over to Sierra Madre. I will generally be riding free in the beginning until I get better at riding fixed.

44/18 should be fine if you dont mind grinding on some climb, but overall you should be good. Pasadena has a bunch of rollers, but that gearing is easily doable

You should be good. I'm comfortable riding 46x16fixed/18fixed in and around Pasadena. :)

i ride 44/16 on my fixed gear. sometimes i think something a little smaller would be good, but not enough to bother swapping.