My boat is thirty years old. It's a nice boat in good condition and I want to take care of it, but it's not a shrine. Am I overthinking this?
In my humble opinion, yes, you're getting lost in the weeds.
If you were racing or were a long distance cruiser where 1/2 knot of lower speed may mean adding hours to your trip, then you would want the bottom perfect.
But your not, your a day sailor and according to an earlier post, you want a relaxing sail. What will you miss more, a little speed or possibly several months of sailing this season?
Don't get me wrong, I'm a do it right the first time kind of guy and typically over think and over do a lot of my systems. The bottom is not one of them.
Each spring I scrap off loose paint and put a fresh coat on with a double coat on the waterline and high wear areas. (this is for three seasons now). Once it's in the water I forget about it. I would rather focus on improving my tools for sail trim. That's where I think I will get the most speed increase for my dollar. When I can get perfect sail trim and still want to go faster I'll invest time and money for a new bottom.
I was in a similar position as you are when I bought my O'day 25. The first fall it was hauled out the yard called to tell me that as the bottom was drying the paint was flaking of the bottom. I checked and sure enough it was. I had them media blast it. It looked a lot like yours with little chips out of the gel coat. This was in the fall.
In the spring I used a non blushing penetrating epoxy for the first coat. Then a little thicker epoxy for the second coat. Neither were true barrier coatings.
Then I put on 3 coats of ablative bottom paint. By the time this was done the bottom was smooth. The bottom paint didn't flake off and I just put one new coat on each year for the next 4 years before I sold the boat.
This was not a by the book solution but it worked for me.
As for letting the bottom dry out, a full winter would be better but you are not going to get warm enough weather to do the bottom until later March or early April. Let it dry out til then. Then plan a simple solution for sealing the gel coat and putting bottom paint on. Three days of good weather and you can have it done in time for launch.