It does indeed make sense. I didn't know that higher timing in resulted in more power though. So the more timing you can get out of it knock free the more power it should make, in theory? Correct or? I'm learning here. I know absolutely nothing about tuning lol.
Head gaskets become a concern past that IIRC.
You just want to be careful with timing, the higher you go the higher the cyl temps/pressure. In one season and on flat terrain you could have no knock, on another season and hilly terrain you may get lots of knock. If I didn't have a tuner I wouldn't run more than 18* year round and just change pulley sizes accordingly. Vice versa if you own a tuner, or you can play a little more.