Re: can I afford to continue sailing
When i first started sailing I had a trailer-able boat. I was astonished at how inexpensive it was to keep and maintain. I learned a ton on that boat, and the whole family had fun on it.
I love the boat I have now, but it an order of magnitude more expensive to keep and maintain it.
I'd consider finding a trailer sailer on the upper end, and find a marina that lets you keep the boat rigged, on the trailer, in a storage area. a little less convenient, a lot less expensive.
And get that larger boat (and slip fee) when the kids are older.