Wahine, if you move what are the prospects of finding somewhere to live, work, sail? would you move somewhere where you already have family or friends to open up a greater circle of friends or would you land in a new town starting from scratch?
Over the last 12 years I've moved from Perth to a town of 10,000, then a very remote town of 600, a sweet coastal town of around 1000 an hour from the city, and now a regional centre on the coast. Each move gets harder as you spend a few years getting settled and making new friends, only to turn it upside down, move and start again. The flip side is that I've seen a lot of the state, I have friends all over WA and I've done a lot of things and been to interesting out to of the way places that many only dream of.
If you want to move to meet new people, see new things, sail new places and you are not inherently tied to where you live due to mortgages or close family ties I'd say go for it. Just don't move thinking that it will solve the man problem. With an average age of 50 in your town? so for every 65 year old there is potentially a 35 year old too

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Have you looked at other options where you are other than organised sport? A town that size is sure to have volunteer organisations like the SES, fire services, volunteer ambulance etc etc. They are a great way to meet people from all walks of life. Some of my longest friendships have been established through volunteering, I've met one or two of my past girlfriends the same way and I've seen a few weddings come out of them too.