Ok...which way should I go with entry lights?

Ok, I want to pick up a small lighting set. I usually shoot natural light, but I have started moving more into some indoor food/product shooting. (well, at least learning and building myself up since I am new to artificial light use)

I have a 430ex. Would it be better to just get an ST-e2, another speedlight, and 2 umbrellas or similar setup.....

Or

Something like the AlienBees DigiBee.

What would I use to sync the AB set to my 5D?
This is generally for smaller setups. No portraits, etc...

The AB's strobes comes with sync cords. You many options to fire them. Sync cord, pocketqizards, or the new wireless setup from AB. I have seen mixed results trying to set up the speedlights in a studio setting with umbrellas etc. If you are really serious about it and plan to do a lot of it, go with a couple ab400's and small softboxs or umbrellas depending ont he type of lighting you are going after.

Indoor food/product shots don't require a lot of light (as long as the products are small). Even continuous light will work fine if you use a tripod. Start with a few cheap work lights with clamps, and go from there.

Save the big $$ investment for when you want to start shooting things that move.

I have a large worklight that I use when detailing my car. It just gets so darn hot and is pretty harsh. Maybe I can find a diffuser panel or something to put infront of them.

Hotlights are a pain in the rear for the reasons you mentioned and more. Strobes are not so mysterious as many people think. Start simple and build. If you are in a studio all the time then ABs are ok. If you are mobile, then an STE2 and another Canon strobe might be better.

Yeah, i would either be in a pro kitchen making a setup, or in my makeshift studio that I would put together for stuff I can shoot on my own without the chef. The price of an St-e2 and another flash are basically similar to a small entry light setup.