What exactly do you mean by "reinforce"? Do i just get some glass and resin and lay it over that spot? Ive never messed with fiberglass before
So a stress crack is a non-structural crack in the finish. The pole has what looks like cracks but they are only in the gel coat. They are not affecting the structure of the pole, just the appearance. They can be a sign of weakness underneath and may reappear even after painting, but your pole or hull probably wont crack or break under normal conditions.
The 4th picture in your original post appears to be a crack. It looks like it may be complete through the hull. How it happened I can not say. The crack will continue to travel down it's path as the ski is weaker now than before it cracked.
Reinforcing is applying new material to increase the strength of the area. Generally you want to reinforce prior to failure, so it's probably more accurate to use the word repair than reinforce, but you may want to consider reinforcing undamaged areas if you expect to continue to abuse your machine.
To fix that crack, assuming that it is as deep as it appears, you will need some epoxy and glass. Drilling a hole in the end of the crack is believed to help prevent the crack from continuing it's path after repair. You will want to make your repair from inside the hull as an outside repair would alter your hood seal in a negative way.
You may need to remove your motor, especially since you are not experienced with sanding or laying up the glass. Sand and prep the inside of the hull. This includes sanding with 80 grit to remove debris and rough the surface to bare glass, then clean with acetone (lacquer thinner first if ever working on an area that had been waxed).
Overlap refers to the amount of material you need past the repair. So if you have a 1" hole but use a piece of 3" diameter cloth to fix it, you have 1" of overlap on both sides and 1" of repair (1+1+1).
I am not an expert on exactly which weaves are the best for which jobs and how much overlap is required. Personally I like 1208 glass with 3:1 epoxy resin. I'd probably do 2 layers of 1208 at 1" and 2" of overlap, maybe a 3rd layer of 1208 or 10oz at 3" overlap. If you are going to reinforce after the repair, do 2 layers for the repair at the same time you reinforce, making the reinforcement the 3rd layer of your repair but 1st layer over everything else.
Again, i'm not an expert on exactly what is the best balance of weight and appearance. I tend to try to over build so it doesn't break again.
Finish up by using a small amount of filler on the outside and some touchup paint. You could consider a thin layer of glass on the outside but I wouldn't put much more than like 4oz where your seal goes.