Bill, Your BO is no worse than mine, I think.
Small sailboats (and don't be unnerved that people call them 'racing dighies' or just dinghies) are a blast and I would guess that more than 50% of those with much bigger boats learned to sail on them. Some of us still own day sailors as well as bigger, more gear intensive sailboats.
First of all, congrats on getting your 'Ugly Duckling' Sea Snark rigged up and working for so little $'s. That is impressive. I would like to see a picture to see how you did it so please post one here or put it in your profile.
Next, I will have a go at your questions:
Question 1: How does a gaff rig compare to a sloop in ease of sail and performance?
The gaff rig is an older and saltier looking rig IMHO but will not crank out the speed that a taller mast sloop rigged vessel will. One reason is that the wind is generally stronger higher up. I have sailed on lateen rigged (Sunfish), gaff rigged (Catboat) and sloop rigged sailboats and the easiest to set up and just go sailing with is the lateen rig as it has the fewest controls. Next would be the gaff rigged, which, if it has a jib should perform better than lateen. The most performance you can get is from a sloop rigged racing dinghy but it is not as easy to do as it can have many more controls and may require hiking out and split second decision making which is more like work (but fun).
Question 2: Is there something close to what I am looking for that is a sloop rig?
Of course there is/are. Tons of small boat designs to choose from. The only question you need to answer for yourself is what you want and whether or not you want to make one of buy a used one.
Question 3: For puttering around a lake does the rig type really matter? I don't see myself really getting into racing, but after reading about travellers, boom vangs, topping lifts, spinakers, and such I may have an inflated sense of their necessity.
Do you have any of this equipment on the 'Ugly Duckling' and haven't you been out sailing on her? No, you don't need all that stuff, it is just fun to have once you get to know how to use it and when (why doesn't hurt either).
You say 'puttering around a lake' so I get the impression that the lake is fairly small (exact location might be interesting). Does your sailing dream include trailering your boat to a bigger body of water one day? If so, your 'inflated sense of their necessity' may be justified.
Question 4: What am I not taking into account?
Do you want to be able to do some overnights on this hypothetical boat?
The bigger the boat, the bigger the headaches and costs (under 20' is still not 'big' but once you throw in a trailer it adds more maintenance chores).
To finish I will mention that I own a 19' Lightning sloop that is rigged for racing. It is a one-class design and has: outhaul, spinnaker & pole, backstay tension rigging for raking the mast, jib 'cunningham', traveler and a vang (I know I am leaving something out). I still haven't rigged up the vang as I do not race with it yet but it sails rather quickly when the wind pipes up and can scare the crap out of my wife in a gust as it heels. This boat cost me $1K with a so-so trailer and 2 sets of sails (fire sale, right place at the right time) and costs me very little per year to sail it. I also am part owner in a 27' Tartan that does not have quite as much running rigging but costs waaay more per year to maintain as it has not trailer and is really not a trailer sailboat at 7200#. Cost per sail on the Lightning is waaay cheaper than the bigger boat but the bigger, heavier boat is safer for going out in 20kt + winds in as it will not capsize in most situations.
Good luck and post a picture of your 'Duckie'.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
Everybody has one:
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