Re: Choosing Type

Before I start, I have to admit that I'm a bit of a type-nerd so I have a long list of resources for this question. I apologize in advance if I take the suggestion you were going to make, but I have trouble shutting up about typefaces. If I had more patience, I'd love, love, LOVE to be a type designer, but I just don't think I can focus on minutiae for long enough to do it. 

So, let’s go backwards through your questions because I think my answers to the later ones will probably affect what I have to say about the first one.

Resources for finding typefaces:

• Hype for Type: TJ put me on to this website last Spring in Words & Images, and I still haven't had a chance to look through everything they have going on. What's really cool about this site is that they have AMAZING sales...sometimes you can get a beautiful family on sale for around $30 for 10 fonts (right now it looks like the sales are at 50%). I also like that many of these faces have a lot of personality--most of those are only in one weight, though, which is clearly an indication that they're designed for headlines, not to be readable as text--and you can easily browse by category. 
• Spend some time on I Love Typography. This guy definitely loves typography. And he has posted some great articles about choosing typefaces, type history, type for the web, the list goes on and on, not all of which I've been able to get through as of yet. So, this site is worth hanging out on for a while.
• FontShop: I've loved this site for years, and they have some awesome resources, including an Education section that addresses a lot of questions relating to typography--again, I haven't gone through all the info here. You can browse by category, here, too, but what's really cool is that you can browse by designer and by foundry, so if you find a typeface that you love, it's easy to find others designed from the same perspective. I've found that, when mixing typefaces, it can take some of the guesswork out if you use two types designed by the same person. Under the FontLists tab, another search option on their site is by function; for example, you can search for typefaces that work well in book design, which might yield a different list than "sports" or "web design."
• Google Fonts: When designing for the web, or for people who don't have the funds for a license for an expensive typeface, I generally come here. The user-interface is super easy (it's Google, after all), especially in terms of collecting fonts for web design--the site will generate the code to include in your CSS. 

As to how to know what typeface is being used in a project, I have a few resources for that, too, but in general, I'd say it helps to get a little type-nerdy and learn about those little, sometimes quite subtle, differences between typefaces. I personally found Ellen Lupton's book Thinking with Type (Amazon) to be a clear, fascinating introduction to how type works; incidentally, the book's accompanying website has some more resources. While it may seem tedious, when you pay attention to the shape of certain letters in a particular face--the capital R, for example, or the lower-case g, and you compare that to another typeface's version of that letter, you do start to recognize the differences. 

• As to resources for recognizing typefaces, Identifont is my favorite. I use the far-left "Fonts by Appearance" feature ALL. THE. TIME. It walks you through some questions aimed at those elements of the letters that differentiate one face from another. It's also a good resource if you have a general idea for a font, like a sans that looks a little like Helvetica but isn't Helvetica, because it can generate ideas for similar typefaces for you. 

Fun things type-related:

• If you have trouble matching typefaces, typeconnection is a type-matching/dating game for typefaces. The site gives you a profile of the typeface as if it were looking for a date, and you try to identify a match for it. In the process, the site reveals a profile for the possible matches, and if you choose a pair that will not have fun together, it explains why. 
• I also quite like TypeFight. It's a project where the designers who run the blog assign a letter form to two other designers, which are then posted side by side, and then visitors vote on which designer's letter they like best. The winner gets bragging rights, I guess. Sadly, it looks like there hasn't been a fight since May. 
• There are probably many more apps out there, but I have: Typography Insight, which Allison showed us in my Type I course and has a lot of information in a clean, easy interface. I also have "I Shot the Serif" and "Helvetica v. Arial," both of which are app games that are fun times with typography. (I did warn you about my type-nerdy-ness.)

In terms of knowing how to choose the correct typeface, I might reframe that to thinking about the best typeface for the project that you can choose at the time. I think part of that is having spent some time learning about the elements of typefaces and comparing them to each other, and then ultimately, it's about choosing something that works within your project as best you can. There's so much information just on these sites that I've listed, and many others that I'm sure people will post, not to mention the books out there about typography, that it may be next to impossible to know everything there is to know about type, or to be sure that the face you choose is the absolute best, which is partly why we draft and discuss and take classes on the subject. 

I also think it's about trying different faces in the context of the project and seeing how it looks. One of the suggestions Allison made to our Type I class that stood out to me, though I don't always have a chance to do it, is to print a copy of the project and hang it on the wall, then look at it from across the room. Obviously, if you're working with sections of copy that are smaller size, you won't necessarily be able to read it, but even then, you'll get a sense of the texture that the typeface has and the color that comes across in context of the rest of the project. And you might recognize that the text you're using comes across too dark and needs to be a lighter weight or that you need a typeface with lighter strokes, or vice versa. Okay, so I'm going to make myself stop now.