Hi,
Your canoe was indeed glassed at some point, and apparently, not very well.
Many of us on this forum are not in favor of replacing the original canvas with glass. When we encounter this, we will remove it as a first step in a restoration. What you do is entirely up to you. If the weight of the canoe (they are heavier when glassed) is not a showstopper for you, you could most definitely sort out the leaks well enough to use it more or less as is.
It looks like someone has painted over the resin so not only are you dealing with a mediocre fiberglass job, you are also dealing with peeling paint or resin.
If you simply want to get into the water, patch those holes with duct tape and go. Do not use anything that has silicon in it to stop leaks, at least not if you plan to try and sort out the glass.
If it were mine and if I were leaving the glass on, I would start by sanding the entire hull with an orbital sander. I would probably be pretty aggressive and try to remove those flaking areas. You do not want to cut into the glass cloth, but you need to remove anything that is loose and oxidized. Once this is done, clean it up (I use acetone) and see what you are dealing with. Small divots like you have shown should be repaired. I would use glass fiber and resin to fill those spots. Areas where there is glass weave showing need to be properly glazed with resin if you want a smooth appearance, but if they don't leak, you can probably live with it.
Once you have the leaks sorted out and the hull smoothed, you may decide to apply a layer of two-part epoxy paint. This should get you a lasting and tough outside finish.
You must be sure that you take care of the wood. It also needs to be sanded and varnished to prevent it from rotting. Several good coats of good quality marine spar varnish will protect the wood. Do not use a urethane varnish.
All of that said, my preference is removing the glass and doing a proper restoration, but that is a time-consuming job and might not be worth trouble. If you get curious about doing a proper restoration, check this site for books that provide step by step instruction and also search this forum for information.
If you made that paddle (cherry?) you should be able to restore the canoe.