Hi Wedger
Firstly welcome to the forum.
See you have a Wilson flyer, a very good stable fishing platform if ever there was one. I used to have a Pilot 17 that is a very similar boat to the Wilson and had loadsa fun on it.
Leeward 18 hum.... I looked at and wanted one of those when they were first produced. Very workmanlike and on a calm (very) calm day with a 120hp diesel inboard should fly for a guess about 30knts or possibly a little more. You will probably find the ride to be very hard, as all boats with no pointed ends tend to bash through rather than cut through the water. On the plus side with the beam being almost the same throughout its length it should provide a stable platform to fish from. To be fair I haven't been out on one, was tempted though and nearly bit the bullet until I saw the Warrior 195, which I finally bought. The Warrior has a pointed end and does cut through the water but unfortunately are no longer made.
I like Adam fancy the Pirate 21 formerly known as the Souter 21. Nice deep vee hull that will give plenty of economic speed and yet sits nicely on the water. If I had the cash I would probably indulge myself.
Regarding pontoon costs.. Up until this year I kept me Warrior on a pontoon berth. I started to trail my boat again, the reason being the cost to keep her afloat went over 2K, from my point of view just a bit to much. When you take into account antifouling, new anodes every year plus the other usual expenses related to a boat living on water it was nearer 2.5K
I am sure you will get many varying views that may only serve to confuse you, but hopefully you can cherry pick the ideas and make a decision that suits you
Good luck
Martin