Alberg 37 or Cape Dory 36
While I agree that both are reasonably visually attractive, (which was the answer that I expected to hear)how a boat looks is only a small component of what makes a good boat. Buying a boat because of its looks is a bit like wanting to marry a calender girl. There are other traditional and attractive designs out there in your size and price range that are better sailing boats.
Both of these boats, like most of Alberg''s designs, derive from CCA racing rule ''rule beaters''. They have extremely short waterlines, narrow beam and a rig that is heavily dependent on large genoas in moderate to light air.
Having sailed on the Ablerg 37, and observed the Cape Dory 36 underway, these are slow, wet, cramped,tender boats that are sailed at large heel angles, do not track well and that are not very good in a chop or quartering seaway.
On the positive side, both offer comparatively shallow draft which is nice and a simple, very workable interior layout. The Whitby built Alberg is nicely construted. The Alberg 37 (at least the one that I sailed on), had undersized winches for the big genoa)
In my book, neither boat make very little sense for someone who is starting out in sailing and who really wants to learn sailtrim and boat handling. That is best done on a smaller, more responsive boat.
With regard to the Cutter vs Yawl rig, Cutters generally tend to be more weatherly (point upwind better)and sail better dead down wind. Cutters tend to have sturdier staying but generally end up with running backstays in extreme weather when snugged down to staysail and heavily reefed mainsail or storm trisail. One disadvantage of a cutter rig is that it more difficult to tack the genoa through the small gap between the forestay and jibstay. My normal advise on cutter rigs is to set it up so that the jibstay can be detached and stored against the mast when in conditions that warrant using the genoa. This really shouldn''t be done on the Cape Dory because the forestay is tacked to the end of the bowsprit rather than the stem.
Yawls really came into being as race rule beaters. Under previous racing rules, the sail area of jibs and mizzens were pretty much ignored in the rating. This popularized the masthead rig and the yawl. There was a bit of a valid basis for not measuring the sail area of a yawl under these rules. On a yawl going to windward, the mizzenmast and sail actually produce more drag than they produce drive. This is because the mizzen is sailing in really turbulent air and has to be over trimmed to keep from luffing which can effectively act as an airbrake.
Downwind mizzens also are a problem. In this case they are forcing the main or foresail to operate in their bad air and so again they are not adding as much to the speed of the boat as they are taking away. BUT in the predominantly reaching races that were typical of offshore races of the era when Yawls were popular they offered a number of advantages. First of all on a reach the sails are not acting in the slipstream of each other and so each contributes a fair amount of drive for the drag produced. Also with the advent of lightweight low stretch sail cloths, mizzen staysails, which are great reaching sails but a fair amount of work to fly (You must douse and raise on each jibe), came into widespread usage in racing.
One nice advantage of a yawl is the ability to sail ''jib and jigger''in heavy air, meaning sailing with just a small jib and the mizzen. Yawls don''t do this as well as ketches because the mizzens tend to be too small and mizzens on yawls are rarely stayed as solidly as one would like.
I also do not consider these boats to be particularly good single-handers. The required use of large genoas makes these boats hard to tack shorthanded. Even with a good autopilot, large genoas are really difficult to tack with one person because you really need to overstand the tack until the genoa blows through the gap between the forestay and jib stay and past the shrouds and then harden back up to bring in the jib.
This is not meant as a put down in any sense, but I would suggest that you spend more time out on the water, and try to sail on a variety of different designs before locking in on just two models. I would also suggest that you start with a smaller lighter boat while you are learning to sail. You may not end up trading up, but even if you do, you will end up a better sailor for it.