Spelunko -
My standard recommendation to people who want to break into sailing ship modeling is: start with a small ship in a large scale. (The Heller Pamir is an enormous ship on a tiny scale.) My reasoning is that large scales are easier to work on - especially when it comes to rigging. And a few weeks, or a couple of months, invested in a small ship pay great dividends in terms of experience when the modeler tackles a bigger one. We've had interesting Forum discussions recently with several people who are wrestling with the Heller Victory, or the Revell Constitution, as their first ship model. Those folks have spent lots of time learning, making mistakes, and re-doing things - i.e., suffering through a learning curve they could just as well have experienced on smaller (and cheaper) models. If they'd started with sloops, schooners, or brigs they'd all have finished models on their mantles by now.
Unfortunately my profound advice is difficult to follow at the moment, because the kit manufacturers don't listen to me. (They aren't alone in that category. At the moment, as a semester at the university grinds to its close, I'm being reminded once again that scarcely anybody listens to me - least of all my own kids. I shall now climb down off that particular soapbox.) The plastic sailing ship kit industry is almost dead, and few kits currently on the market represent small ships on large scales.
The Heller Nina, Pinta, and Santa Maria aren't bad, though they're old kits and pretty basic. (Be aware that the Nina and Pinta use the same hull. At least half the kits in the Heller sailing ship range are based on recycled parts.) Our knowledge of those ships is so meager that a modeler trying to depict them can get away with a lot. The problem is that, as usual in Heller kits, the instructions are miserable. Those kits could be made into nice models, but to do so would take quite a bit of research - in books that probably aren't easy to find in Taiwan.
Lindberg is currently selling a number of very old kits (1950s vintage) that were originally produced by the now-defunct American company Pyro. They aren't the most sophisticated kits in the world; in fact they're extremely basic. But they're reasonably priced, the overall shapes and proportions are right (which can't be said for many of the Heller kits), and they're good bases for dressing up with aftermarket parts. (We're talking about vessels with two masts and relatively few sails, so the number - and price - of the aftermarket parts would be minimal.) And several of them represent relatively small ships on relatively large scales. Unfortunately Lindberg (following Pyro's lead in what I gather is a simple marketing ploy) has put deceptive labels on them. Pyro's American Revenue Cutter Roger B. Taney is being sold under the name "Independence War Schooner" (which makes no sense whatever), the American Revenue Cutter Harriet Lane carries the label "Civil War Blockade Runner" (ok; the Harriet Lane got captured by the Confederacy and did run the blockade a few times), and the Grand Banks fishing schooner Gertrude L. Thebaud is currently labeled "American Cup Racer" (yeah, right - a racing yacht with two stacks of fishing dories on her deck).
Any of those has the potential, with a little work and, perhaps, some aftermarket fittings like blocks and deadeyes, to be a nice, attractive model of a significant ship - and could be completed in weeks rather than months or years.
The Squadron website is advertising a new kit from the Russian manufacturer Zvezda that really interests me: a medieval cog. That's a single-masted merchant ship, with "castles" on the bow and stern. I haven't seen the kit in the flesh, but if the box art can be believed it's likely to be pretty good. It's on 1/76 scale (presumably to match the numerous boxes of nicely-detailed figures that are available from Zvezda and several other companies). It strikes me that this one, if it turns out to be any good, would be an ideal newcomer's project. It would offer all sorts of opportunities for color schemes (and "wood grain" effects) and, with its single mast, just enough rigging to give the modeler some good experience without much repetition. I'm thinking of getting one and installing a small CD player in the base, to play excerpts from the first act of Wagner's Tristan und Isolde. (That would surely be some sort of first in the ship modeling world: a model that plays opera.) Unfortunately the price is high: about $75 in the U.S. But it might be worth a look.
The ideal "starter" sailing ship kit would (1) represent a relatively small vessel, (2) be on a relatively large scale, (3) be reasonably priced, and (4) be in the current catalog of a manufacturer with a good international distribution system. Unfortunately I can only think of a handful of plastic kits that meet all those criteria. (The picture is much better in the world of wood ship model kits - but that's another story.) Maybe some other Forum participants have some other ideas.