You asked,"You said that you tend to foot. How to you judge footing versus pointing?"
I do not really consider myself a footer. If I have to then fine, but I stay more in the middle to the high side. The reason is that I sail a bit light compared to others.
I presume you can tell if you are sailing with others whether you are pointing more than them or footing, so I will talk about when you are the only boat you can judge from:
Pointing, also called pinching, is when you are sailing along to the weather mark and you point the boat more toward the weather, upwind. Do so until you feel the boat slow down just a bit. Then crack off slightly until you feel that you are moving through the water more than you are stalling. It takes a very fine touch to be able to sail a whole leg this way, and it is exhausting on the brain. There are not many times that I would recomend sailing this way. If you are under someone before the start and you do not want them there, you can pinch to make them go away. That may be the only one that I can come up with.
Footing is when you sail to a point that feels as though the boat will not stall and pull the tiller down a bit more. You will feel a bit of acceleration. If you are sailing in about 15 MPH winds you will be double trapped, have to downhaul pretty seriously and maybe even crack the main and/or the jib occasionally. That is if you and your crew are 315 lbs on the boat. If you weigh more and you are not double trapping you should consider footing to get to that point.
By the way 15 MPH in my area is when there are whitecaps. I sail mostly on the Pacific Ocean and the swells are normally 1 to 4 feet.
I think it is much easier to foot as you will be able to keep speed up and the groove, little variance of the speed of the boat, is larger to sail in. Of course you cannot just reach around the course to weather, so do not go overboard. The Tiger is a good boat to foot in two circumstances. Right off the start line for a bit, it will get you moving nicely, then you can trim the boat and sail the sweetspot. Another place to use it is to make sure that there are no boats that can tack on top of you for the weather mark. Being a little conservative there by overstanding does not hurt much, if at all.
The rest of the course should be sailed as close the sweetspot, not pinching or footing, as possible. Always look for pressure. If you are not on a lake, which I do not understand, sail toward where the water looks darkest, due to wind.
Hope this answers your question,