A Zoom, A Flash or ???? - What to get next?!?!?

Hi All,
I'm trying to prioritize my next Photographic acquisition and
am facing a list of equipment holes that doesn't line up at all with my current budget. (Sound Familiar!) I'm currently 'day job' hunting (ie: unemployed) and simultaneously getting a freelance business rolling. I had a small sum in the ol' 401k that is on it's way to an IRA to mainly get drawn to pay my 'cobra' costs. With the Photo Business starting I recognize I'm seriously deficient in multiple equipment categories, at least to 'my' standards. Which 'Hole' do you, in your opinion(s), think I should fill first?
This is a 'Call for Ideas' kind of thing. I've been accussed of being a High IQ kid and must admit that a fair percentage of the time I'm guilty as charged. I'm also not a 'Kid' anymore either! I like input and exchanging ideas and information. I'll definitely make up my own mind, but am unafraid to say I'm unsure or don't know when it's the case. Right now, I'm unsure of my best option and I don't quite know how to choose.
If funds were 'reasonably' unlimited, I'd acquire immediately: a 17-40L, a 430/580ex flash, A 5D, and a 70-200L as the 'core' of a terrific imaging outfit. I would also rank them in that order of priority of acquisition in the presence of Limited Funds. For the record, I'm not a 'L' snob or anything - a) they're the lenses that ergonomically felt the best in my hands and they SCREAMED to me 'Lets go take Pictures!' when I was handling them at the shop. b) The Image Quality I've seen posted in the samples and the tests on PhotoZone.de kicked butt c) A+B=C [Buy those two lenses first]. (OH! I just remembered - I'm rough on equipment chasing images and the L build quality would be nice)
I'll List a little fuller my current equipment next, but what would YOU buy first to be out doing very general photo work for pay? I'm not chasing any Wedding work - It has never felt 'me' when shooting the Posed stuff and mandatory group shots etc. I am getting fairly good response to probes of doing Broad Based/Small Jobs for local realtors, factories, businesses, and such. I'm business modeling for a job a week kind of thing if I've got a 'day job' and much more in it's absence. I won't really know what I'll be encountering from job to job. I'm envisioning building a good General Practicioner Kit. (Kind of like a Doctor's Bag she keeps in the trunk.)
Please kick some responses or private messages out there for consideration. I'm up for answering questions, discussing philosophies, etc. (To much free time and quite eager to spend some in intelligent discourse (gotta use those big words once in awhile - I'M BORED!)
Quite Sincerely,
Richard W.

Equipment: 20D, a Canon 22-55USM Zoom (not very good IQ outside mid apertures and definitely not in the edges or corners). A Tamron 28-200 Zoom (1st version - sharpish, but functionally unuseable in to many situations). A Zeiss Pancolar M42 50mm f1.8 Lens on an AF confirm adapter (very nice image quality, but not 'easy' like a Canon 50mm f1.4 USM would be, yet several magnitudes less expensive!). To make things interesting, I have a set of M42 extension tubes to use with the Zeiss 50. (still learning how to 'use' them). I have NO DEDICATED FLASH at all. I'm capable in the old school ways and use a smallish vivitar auto flash on camera and have a monster Sunpak Grip Flash awaiting confirmation of hotshoe safety (I have information about x synch voltage in older flashes frying motherboards, but am confused about whether this applies to the hot shoe, as well.). Relatedly, I have a sekonic ambient/reflected/flas​h light meter. For camera Support I have a Stone Solid Tripod of 60's vintage FULLY stable extended to six feet (I got it for my 4x5 Camera years ago.) In addition I've got a Bogen Monopod (headless) that I dislike using - which is because it's headless I believe! I am seeing a pistol grip in it's future. I also have a wonderful & just acquired LowePro shoulder bag (it has much more room than I have AF equipment! - It's begging to be filled!).

Wish List:
Dedicated flash, off shoe cord, Macro Ring Flash, A good zoom for using on both a Crop and a FF - the 17-40L seems most logical, a switch hitting long zoom - 70-200L (Non-is, but Definitely IS if $$$ is AT ALL available at time of purchase). A 5D body ( I have a sense of creativity that looks for the image in the scene, be it W_I_D_E or TELEPHOTO and I'm just looking to capture that certain something about what I'm seeing that makes me 'like' what I'm seeing. (if that makes any sense) I'm a Generalist kind of image maker, I'd say. I would have bought a 5D in the first place in order to get the wide angle ease of use and my tele world doesn't go much beyond 2 or 3 hundred millimeters, but you can't get a '5' for the 175.00 I got my used 20D for.

Dude, There's too much info here...I got through about 1/2 your post....Quickly, in black font...In less than 40 words...what do you want help with

[QUOTE=ZeissFan;501763​1]Hi All,
I'm currently 'day job' hunting (ie: unemployed) and simultaneously getting a freelance business rolling.

I understand. I hunted for a day job for along time before I decided that I was just going to do photography.

If funds were 'reasonably' unlimited, I'd acquire immediately: a 17-40L, a 430/580ex flash, A 5D, and a 70-200L as the 'core' of a terrific imaging outfit. I would also rank them in that order of priority of acquisition in the presence of Limited Funds.

Funds are always limited because of scarcity. Giving us a real budget instead of vagueness would help tremendously. I have no reasonable standard to determine a bright line as to what 'reasonably unlimited means'

I'll List a little fuller my current equipment next, but what would YOU buy first to be out doing very general photo work for pay?

Here is my setup. I do a lot of freelance work for newspapers and magazines. I also do work on album covers and some art director projects.
Canon 1D Mark III, Canon 85mm f1.8, Canon 50mm f1.4, Canon 70-200 IS f2.8, and Nikon 18-35 f3.5-5.6, 2 Alien Bees B800, Stands, Pocket Wizards, and the other necessary accessories. For day to day freelance work it is a great kit.

I'm envisioning building a good General Practicioner Kit. (Kind of like a Doctor's Bag she keeps in the trunk.)

Thats what I do for the most part look above at what I listed. It can get me great shots in almost any environment.

Wish List:
Dedicated flash, off shoe cord I dont care for off shoe cords I like Pocket Wizards, Macro Ring Flash, A good zoom for using on both a Crop and a FF - the 17-40L seems most logical Its a really nice lens, a switch hitting long zoom - 70-200L Get the is you will regret it later if you are in a venue where you can not fit a tripod and wish to use slower shutter speeds.(Non-is, but Definitely IS if $$$ is AT ALL available at time of purchase). A 5D body Its a great body but to me not the most suited to a wide varity of shooting that freelanceing can often require. I often do not shoot in the best conditions and like a more weather sealed body but hey this is really up to you. You can get amazing pictures with any body.