I mainly do nature and landscape photography, but I find I am increasingly recruited by friends and family for photo projects indoors. Just playing around with flash gave poor results, so I am trying to build my flash skills. I have read the Strobist 101 and 102 series, as well as the Hot Shoe Diaries by McNally. For equipment I have a Canon 5D with 430EX flash, ST-E2 controller, Omni-bounce diffuser, a 5-in-one reflector/diffuser, and Demb Flip-it.
I seems like the next step is to get a light stand, umbrella adapter and an umbrella. Lastolight now sells a stand, adapter and 5-in-one umbrella along with a shoulder bag to fit it all in as a kit, would this be a good starting point? Should I just go to my local camera store and get a generic set-up? I figured this set up would hold me as I save for the 580EX (yes, I know Chuck!). Any other advice??

Would I be better off starting with an umbrella, or an Ezybox Hothshoe?

Either a small softbox or an umbrella are fine to start with. The important things are:

1) Understanding how light works (Basics; angle of reflection = angle of incidence; balancing relative light levels to create different effects; controlling contrast (light to shadow fall off pattern) through light placement and especially relative size of light source to subject area).

2) Play. This includes move your lights around -- in and out toward your subject, at different angles to the subject, including high and low, and withthe light pointing directly at or slightly away from your subject.

3) Make some quick notes or sketches of how you have set up the lights and keep these in a small loose-leaf notebook.

You should go back to your bookstore and pick up a copy of "Light: Science and Magic (current edition) and "Matters of Light and Depth" by Ross Lowel.

There are two basic ways to create soft lighting:

Big Key Light: A big key source used close will wrap around whatever is casting the shadow. It does the job of a key light, create the highlight / shadow pattern, then also tries to do the job of fill (control the tone of the shadows). Depending on key light distance the shadows may retain a dark core in the areas the wrap doesn't reach. Supplemental fill can be added to lighten the core shadow (second light or relflector) but the shadows will still remain two-toned because the net result is the sum of the overlapping sources.

Key overlapping Neutral Fill: Here a fill light is placed over the camera where it will illuminate every nook and cranny on the front of the face the camera sees. By adjusting its power the shadows can be independently made any tone desired: light for a soft look, dark for a harder look. Because fill already has lifted the shadows as desired for the mood of the shot, the key light overlapping it doesn't have a need to wrap and do the secondary job of fill. All the key light needs to do is create contrasting highlights on the higher parts of the face. Our brains equate highlight with high and shadow with low because that's how natural light which comes from overhead illuminates the world around us most of the time.

Both are to means to the same end: soft lighting. The advantages I find in the second approach is that is allows me to dial in whatever level of softness via fill and use smaller modifiers to achieve "soft" or "hard" lighting. The advantages of the second approach are obvious to me because I learned flash using two bare unmodified flashes in the same key overlapping fill sources from a master of lighting to shoot wedding receptions where carting around umbrellas just wasn't a viable option.

So given that you can't swing the second flash now I'd suggest adding white umbrella to what you have to get a big source (option one) for minimal outlay of cash. That will also give you a chance to try and validate the cause and effect I describe above. If you go the softbox route you'll have a single smaller source without the wrap of the larger umbrella and may find it difficult to get your reflector where it can catch its light and put the fill were it is needed the most, the key light shadows on front of the face the camera sees.

Whether or not to get a second hot shoe vs studio lights comes down to what you will get the most use from. I have both but use my Canon flashes 10x more because I don't shoot portraits for hire, and do mostly PJ-style location candid or less formal portraits the pair of hot shoes work for. With the two flashes option two works well with my DIY modifiers for most things. I use an umbrella when I want more wrap or spill: white for portraits of people; and silver for more specular highlights and a stronger illusion of 3D in fur, feathers and beaded gowns.

Chuck

Thanks, this is a great help.

When I read RFI I thought your post was about Radio Frequency Interference and not a Request for Information, but if your experiments take into the realm of radio triggers ( I read that you have the ST-E2 now ) stay away from the eBay gadget infinity stuff or you will be dealing with the bad kind of RFI. Along those lines, if you you are thinking a second light and eventually a third and you don't mind setting them manually you can get Canon 540ez's used for about $90 and the produce just about as much light at the 580ex (guide number 54 at full zoom vs 58). When you consider you can get a decent set of triggers for $200 (1tx and 2 rcvrs) then for about $300 total you can add a second high output manually controlled flash to your setup and a third for about $160 more. Obviously, Strobist is the authority on all things off camera speedlight related so you should read up there.