As a beginner, would you recommend buying new gear or used? I don't know what to look for, how much things are worth, or anything, so I'm hesitant about buying used, even though I could probably save some money that way.

Are there any retail stores (Orvis) or brands that I should stay away from? (rod, reel, line-wise)

Are fly fishing guides useful for a beginner, or a waste of money?

I would start by attending either a Cabellas or BP casting class, I started with a cheap rod and reel combo and have advanced to a better one although not that expensive. Where are you located at?

you wouldnt save that much on used, you can get started with a 150.00 rood & 50.00 reel and 60.00 line , so thats 210, figure in 20 to 50 for flies & your good to go.

look online at Cabelas & Bass Pro fly stuff, they can give you a decent idea of what your looking at....you need to decide if you are gonna pursue Bass, Sunfish, Trout (gotta go outta state mostly for that) or salt...everything is geared towards your prey...I fish bass so I used heavy rods & lines, a fly reel is the least of your concerns as far as actually using it to fight a fish, its more for storing line.
everybody sells pretty decent stuff, I think its harder to buy bad equipment than very good, but again choose according to your prey, example : TFO makes a nice rod called the BVK, and its a dandy rod , fast action but it has no lifting power, in fact if you try to lift a fish with it it will probably break, it's designed to cast well & wear the fish down then land with a net. The rod I use for Bass (this isnt recommended but its what I do) many times I get them near the boat & lift 'em in, but I am using a rod with lots of lifting power in the tip

If you can afford it a guide is damn good way to shorten the learning curve, get one that fly fishes & is a certified casting instructor & you can get way ahead in the game pretty quick, if not then at least take a few casting lessons now so you don't have bad habits later (btw-you can catch fish with bad habits, I do it all the time)

These gents are correct. You need to spend some time with someone who understands and can teach the fundamentals of casting. If you can't cast very well, fly fishing just isn't very much fun. You don't have to be able to cast the whole line down to the backing, but spending five minutes trying to get ten feet of line out there is going to make you hate it pretty quickly.

There just isn't that much used fly fishing equipment around this part of the world, so you'll probably end up having to buy new. Resist the temptation to buy a 20 dollar combo kit from Wal-Mart and instead look at something like the Three Forks combos from Cabelas. That's where I started and I still use some of those rods today.

If you haven't already, read the FAQ at the top of this forum. There's some great information there.

Good luck and let us know how it goes.

Is this a good rod to start out with? I'm thinking about getting it in 9' 5wt. What kind of reel and line should I get to go with it?
http://www.basspro.com/White-River-Fly-Shop-Dogwood-Canyon-Fly-Rods/product/15190/

Or is there a rod/reel combo I should check out?

That's a fine start. There are Dogwood Canyon combos available

http://www.basspro.com/White-River-Fly-Shop-Dogwood-Canyon-Preassembled-Fly-Outfits/product/96504/

I started with a cheaper combo and then moved up to this one in a 9" 5wt comes with line and everything.

Cabelas Fly Combo

I've got gobs of used rods at used peices on my blog; fiberglass and graphite. I can fix you up with a reel also. I've been fly fishing for 50+ years and I always buy used stuff; nothing wrong with it; fly men are never satisfied; always wanting more stuff; there's some bargains in used equipment, but I have to also say that bas pro, cabelas, and other major outlets have some cheap equipment that is very good. TFO has an entry level rod that is hard to beat for the money-p-

I have 3 of these and have been very happy! If you keep an eye on the website, they run them on sale pretty often also. For a few weeks late last summer, they actually had several size/weights of this on sale for $39! That's why I have multiples! LOL

If you get a short lesson such as the free classes that BPS and Cabelas offer before buying anything, it would help you make a more informed decision on what to start with. I realize this is not an option for everyone, but many people do not realize that you do not have to bring your own equipment to most classes.

Good luck!

My Grandfather taught me how to fly fish he had me spend hours on the front lawn practicing my cast way before I ever got to hit the water with a fly, My first rod was a cabelas first cast rod 8' 5 WT and personally think its a really good training rod to learn on I have taught my brother and sister on that rod and using it they both picked up on the fundamentals rather quickly and easily with it and its durable to boot mine is now inching out 10 years and looks almost perfect save a ding on the reel here or there from people falling while carrying it lol

eBay is your friend, I just bought a spool of brand new scientific angler sharkskin line (99.95) for 49.95. I find a lot of good deals on things there.