Greetings from the great white north

This is my first post. I decided to "join" after spending several hours pouring over the wonderful information that is available from others. I was lucky to become the second owner of an early 1970's Day Sailer three weeks ago and with the help of a couple of friends who are seriously experienced, I have been out several times now. I live in northern Ontario (Canada) on the water. My lake is about 8 Km long and 1 Km at the widest. It is a typical narrow Cambrian Shield lake that is oriented east/west, and the wind regularly blows from west to east. My boat is the second sailboat on the lake and (thankfully) we only have two PWC's and a couple of party barges to contend with. The other sailboat is owned by a very helpful retired gentleman who has a 15 ft. Sirocco. He has mentored me on my outings and I have learned by attempting to duplicate his actions.....he leads in his Sirocco and I try to keep up in the Day Sailer. Below are a couple of newbie questions.....any feedback will be much appreciatied...
1. Like many others, I have a slow leak from the gasket. This boat was stored covered, but outdoors, for many years. Is there any chance that this leak will stop (or reduce) over time now that the hull is in the water and the keel is being raised and lowered? Or should I just get on with it and replace the gasket?
2. Living in northern Ontario does have its disadvantages......October will come too soon and I will need to store this treasure safely. It was an herculian task to get her launched so she will have to be stored at the shoreline. One of my summer projects must be to plan for this shoreline storage. Are there any members who have successfully developed a strategy for safe winter storage at the water's edge in a frosty northern setting? (With aplogies for mentioning winter in June!)
Thanks for any advice,
Marv
1. Like many others, I have a slow leak from the gasket. This boat was stored covered, but outdoors, for many years. Is there any chance that this leak will stop (or reduce) over time now that the hull is in the water and the keel is being raised and lowered? Or should I just get on with it and replace the gasket?
2. Living in northern Ontario does have its disadvantages......October will come too soon and I will need to store this treasure safely. It was an herculian task to get her launched so she will have to be stored at the shoreline. One of my summer projects must be to plan for this shoreline storage. Are there any members who have successfully developed a strategy for safe winter storage at the water's edge in a frosty northern setting? (With aplogies for mentioning winter in June!)
Thanks for any advice,
Marv