Sailing on one sail alone
I personally do not believe you will damage a rig by sailing on a single sail, either main or headsail. I also think it useful to experiment with your boat and get an idea of what kind of performance and handling you get with only one or the other sail up. My H28.5, for example, will sail quite well with either sail alone when the wind is over 10 kts. I sometime just use the genny when the wind is really blowing, I'm alone, and I'm not looking for a struggle. The only potential problem I've encountered is not maintaining enough boat speed (my fault) when starting to tack in order to get the bow through the eye of the wind. If that happens, you can just fall off, build speed, and try again, or -- if you are lazy like me -- you can "wear ship" and go 270-deg around the other way to come up on the heading you want. Whatever works, works.