Unfortunately it looks like the landlord is using the approach of legal attrition to force the sailing club to go bust due to legal costs. Not a lot that can be done if he has deep enough pockets to drain them of their reserves.
Red fox 200e - Twin dagger boards which don't take up cabin space, sits on its bum, so dries out nicely. As others have said depends on what you can tow. I have a micro 18 class boat, but it has a lifting keel a bit like a topper. weights under 750kgs so easy to tow.
Maybe check the small print, there was a post recently on the mobo forum where recovery was refused as they decided the trailer was not in roadworthy condition, (a wheel had come off!)
Bought a New to me Boat and the Wheel Fell Off
While this is true of roller taper bearings, many braked trailers are now fitted with Alko hubs, which use a sealed bearing, which has to be pressed into the hub. These are a pain to change at the roadside...
The one I linked it is what I swapped my keel winch over to (different boat to you). Its design means you can let go of the handle and it stops where it is, simply wind or unwind, there is no freewheel!