As I've mentioned before, one of my principal reasons for going to furry cons is to go shopping, and buy art. In recent years, this has exclusively included commissions, I don't really collect prints anymore unless they're big enough to frame and hang on the wall (hint hint, for all you artists out there, consider trying large-format prints).
Now, in the past, I've pretty much only purchased art at conventions, because I felt I didn't have the money at any other time of the year. At MFF this year, that wasn't the case, but I still haven't really gotten any commissioned art outside the con (though, stuff I commissioned at MFF is still trickling in). This isn't because of a lack of artists I know of online, but rather because I really prefer to see the artist in person, chat a bit, and so forth, before having a business transaction with them.
See, the thing I've noticed at big furry cons is that, for the most part, the majority of the artists have about the same skill level. There are those who are notably above-average, talent-wise, but for everyone else (particularly those who are in the Artist Alley at Anthrocon), no one is "bad". And, with the exception of a very few (like Diana Harlan Stein, who has a large banner behind her table), most artists at cons don't have much to set themselves apart from the rest.
This creates a situation where one can easily spend an entire con just browsing artist tables, carefully evaluating each artist for commission potential (something I did once), or spend ridiculous amounts of money getting small commissions from every artist that strikes their fancy (see Orion, the guy with the jacket o' conbadges). Personally, I prefer to only get commissions that help establish my character somehow, rather than getting a million generic poses (or a million random, unrelated outfits/scenes), and now that my characters' appearances have been well-established, those commission ideas require a lot of thought to write down. And, when I do come up with them, I don't want to give them to artists who are likely to screw them up.
So, I've begun to evaluate potential artists to commission based on their professionalism. I look at their style and such too, of course, but what catches my eye is how they conduct business at the con. I have no problem spending lots of money on art, but I want to know that I'm actually going to get something for my money, in a reasonable amount of time (ie, if someone says it'll be done by the end of the con, I get a little concerned when it's not done 6 months later). I understand that creativity can't be rushed, and I never pressure someone to do art for me. But, at the same time, the moment that money is exchanged, this becomes a business transaction, and there are certain things ways to conduct business.
One thing that, to me, indicates an artist's professionalism and confidence is their pricing. Furry art is already ridiculously underpriced, so when I see someone charging $5-10 for a sketch, I don't think "wow, that's a bargain", I think "they must be new". Everyone has to start somewhere, but when I look for an artist to commission, I want the best quality I can find (ie, the best return on my investment), and I want a safe investment, someone who's not going to take my money and disappear. So, when I see an artist's rates starting at $30-40 for full-page work, I see an artist who's confident in their abilities, and who's probably a safe investment. I also don't understand how some furs can consider anyone charging less than triple-digit prices "overpriced".
I also rarely buy art from an artist without a recommendation from someone who's commissioned them. Out of all the art I've bought over the years, the times I've had trouble with communication or slow delivery (defined as more than six months for work that was promised to be done during or shortly after the con) have been the times that I commissioned someone I had never heard of. On the other hand, I've never not-received art I paid for, in over five years of convention-going, nor have I ever been disappointed with a paid commission (except for once, but that was a fluke), so I guess I'm doing something right.
And, since I don't get a lot of art (relative to some), I try to get art from a wide variety of artists. I get a lot of first commissions from various artists, but not many seconds. If I go to an artist for a second piece, it means I loved the first one, and loved dealing with them; and typically, the second commission from an artist is a more meaningful one than the first, one that I'm more worried about someone doing wrong. If I go to someone for three or more pictures, they're one of my favourite artists, and I trust them with very personal, meaningful commissions (like this one). I also try to avoid badges, because I already have more than I can wear at any one time, and I really like the ones I have.
Anyway, just some thoughts regarding my approach to getting furry art. Most of this doesn't apply to online commissions, a concept I'm still getting used to; as a rule, I never buy art online unless I know the artist very well, or I have an excellent recommendation from a friend regarding their methods of conducting business (a simple "hey, so-and-so is a good artist" doesn't cut it for me, lots of people are good artists, I want someone who's also not going to rip me off), regardless of their pricing or how long they've been doing this. Unlike at a con, it's easier to look at an artist's prior work and such online, so the $5/sketch artists are easier to notice, but I still won't spend a single dollar on art outside of a con unless I've known the artist for awhile, or someone I trust recommended them to me.
I hope this post doesn't sound too elitist or anything. I love art, and I'm not biased against beginning artists or anything. This post's content only applies to my thought process when considering furry commissions.