There is, of course, no simple answer to that question. Different strokes for different folks; some people find the leap from plastic to wood is enormous - if not downright impossible. Others don't have much trouble with it. My own opinion, for what little it's worth, is that much of the "mystique" surrounding wood ship models is sheer mythology. What follows is more personal opinion; take it for what it's worth, and for heaven's sake take what I say in context with what anybody else offers.
The wood ship model kits currently on the market fall into two categories. There are, to my knowledge, four manufacturers producing wood kits that deserve the label "scale models." Three are American: Bluejacket (www.bluejacketinc.com), A.J. Fisher (www.ajfisher.com), and Model Shipways (distributed by Model Expo: www.modelexpoonline.com). The other is British: Caldercraft, also known as Jotika. I've never actually laid eyes on a Calder/Jotika kit; they're scarce, and extremely expensive, in the U.S. (The Jotika 1/72 H.M.S. Victory costs over $1,000.) The American firms offer solid hulls, plank-on-bulkhead hulls, and, in a few cases, genuine plank-on-frame hulls. These companies offer a considerable range of American and European ships. They generally come with well-drawn plans, and include reasonably high quality wood parts (usually basswood - not the best of modeling woods, but pretty good) and reasonably accurate fittings (usually either cast britannia metal, turned brass, or photo-etched brass). The prices run from about $40 to $600 or thereabouts.
One problem that newcomers often have with those kits concerns the instructions. The designers tend to assume that the modeler can work from a set of plans; the plans in the American kits are usually pretty good. But the accompanying instructions can create headaches for anybody who doesn't have any experience with such things.
Calder/Jotika kits are of the plank-on-bulkhead type. According to the reviews in the magazines, Calder plans and instructions are quite good. (The company does offer an H.M.S. Bounty, but I wouldn't recommend it as a first effort to a newcomer.)
Then there are the firms that I call the HECEPOBs. (That's Hideously Expensive Continental European Plank-On-Bulkhead.) They include such outfits as Mamoli, Corel, Euromodel, Amati, Sergal, and probably a few others that I've left out. Serious scale ship modelers, almost without exception, regard these...things...as overpriced trash. They're characterized by miserable (or non-existant) research, ludicrous historical inaccuracies, incompetently-drawn plans, generic instructions (sometimes translated into English, sometimes not), mediocre materials, and shoddy fittings that are recycled from kit to kit with little if any regard for accuracy. I've ranted on the subject of HECEPOBery quite a few times in this forum; in the unlikely event that anybody's interested, a forum search on the word HECEPOB will lead to quite a bit of nasty language.
I should offer one big caveat: I haven't by any stretch of the imagination examined every kit from all the HECEPOB companies, and I'm sure there's some variation in quality between them. I have the impression that one HECEPOB company, Amati, has seen the light recently and discovered what a scale ship model is. The Amati kits of the "Victory Models" range seem to be genuine scale models (designed, as I understand it, by a gentleman who used to work for Jotika). Personally, though, I've never seen a kit from any of the aforementioned companies that was worth taking home from the hobby shop.
When people ask me how best to get into wood ship modeling, I always make one big suggestion (which usually gets ignored): start with a relatively small ship, with relatively simple rigging, in a relatively large scale. The Model Shipways Phantom, for example, is a fine basis for a really handsome model that doesn't require an enormous investment of either money or time. In the "Group Builds" section of this forum you'll find a thread by several folks who are currently working on that particular kit. It has a machine-carved solid basswood hull, britannia and brass fittings, and an excellent set of plans by none other than George Campbell, one of the very best. Model Expo also offers, via its website, a "practicum" that covers almost all aspects of building the kit. And at the moment Model Expo is offering a special deal: buy the kit, along with a set of tools and paint, for a quite reasonable price, finish the model within a certain period, and ME will send you a gift certificate equal to the whole price of the package. That's a hard deal to turn down. (Disclaimer: I don't have any affiliation with Model Expo, and would like the company a lot better if it didn't also sell lots of HECEPOB kits.)
That's my opinion. Others probably will disagree; so much the better.