I have found of late that transient mooring is getting harder to find. I used to get it at my marina but now that they have a wait list I have to pay annually to reserve my 30' slip or it will be sold to the next person on the list willing to pay annually. So much for that saving!
Still, when the day comes that I decide to divest myself of my trailerable, I can give up the slip, (and associated costs) tow it home, and sell it from my driveway. I store it in my driveway through winter (snowy) anyway because it is safer there and I can do spring commisioning from my garage.
The mast is deck stepped and very easy to raise with the accompanying mast raising assembly.
I will be bottom painting very soon and will do that in my driveway also, it is very convenient to do boat maintenance in my driveway.
I can also trailer launch in very shallow water with my retractable daggerboard and rudders, or pay $15.00 for the 4000# rated sling lift (not travel lift) and raise the mast on the water at my slip. (I own a MacGregor 26M)
There are advantages to a trailerable if you have your own property to store it on and your own tow vehicle, but once you have to rely on others you might as well just get a regular keel boat with slip and eat the cost.