For the example you use I go for building one totally authoritative page and keeping it up to date. Surely they can only be one "ultimate" guide to grilling steak! You want this to be the definitive resource for anyone interested in the topic. As soon as you start having yearly pages you're going to risk competing with yourself.
And besides, what's better for the visitor? Aren't they going to be confused by multiple pages?
Having a constantly updated resource like this can really grow your authority over time. Find ways to encourage comments / shares and even user generated content. (Can you get review/testimonials) to support the methods described on the page etc.
On a resource page that I maintain, I also make sure I keep the published date updated. That way both visitors and google can see that not only the most comprehensive guide, but also fresh and updated. (I'm getting quite a few searches for "{topic} 2013".
If the page is changing frequently it can help regular visitors if you keep a change log (with dates!) at the bottom of the page so they can quickly find out what's new.
Do you experience seasonality in your niche or does your get stale quickly with time? If say you had a page covering the annual popularity of steak recipes (for example) then I'd probably take this approach:
I'd have a a "Top 10 Steak Recipies" page which I'd update every year with the latest version. The previous years post would be renamed/reposted as "Top 10 Steak Recipes in 2012". I'd then link to the latest version from each old post.
The key here is to make sure you maintain the URL for your main Top 10 page.
This way it will continue to earn links, shares etc over time. The latest version becomes the most authoritative version, but the previous versions are still there for anyone that's interested. (This assumes that the topics past history is something people care about!)
If you're not maintaining a consistent URL for your main post you'll be starting again from scratch every year.
With regards to your second question - yes a single definitive resource page can work, but it's going to depend on a bunch of other factors. For instance, do you have a big, well known brand with a massively authoritative site sitting at the top of your SERPS!
By having just the one hyper-specific one/two page site you're narrowing the topics/keywords your going to be competing for and potentially limiting the reach of your site. If there's traffic there and you can compete then maybe this is exactly what you want to do - but it's a bit like having all your eggs in one basket.
A safer bet is probably a broader site, but keeping the pages specific to particular subjects but again this depends on the resources/time/money you have to develop and maintain content for a bigger site.
What are your goals for the site? What is the website going to have to do to satisfy both your goals and those of your visitors? It can be tough to do that with a one-pager. Who are your audience and what do you need to do to reach them.