Initial Module Ideas

VCO
With my Moogs, I already have several analog VCOs. I'm considering adding something digital (like Plaits). But I really like the sound of the Make Noise STO which is why, at the moment, I'm considering both.

yeah you'll probably want a. couple of these (at least) at some point and a wavefolder and some dedicated utilities - especially as you mentioned west-coast - ie additive, not subtractive synthesis

the newly announced (but not yet available) tiptop buchla 259 might be a good option in the future...

VCF
As with VCOs, I love the Moog filters but already have four in my semi-modulars, so I don't need another basic east-coasty VCF - I think? The Make Noise QPAS seems like an interesting choice to me and I imagine it pairs well with the STO. But I'm open for suggestions.

doepfer make a number of interesting (& inexpensive) clones of classic filters - I particularly like the wasp and the SEM

Modulation
I'm considering starting with Maths and an LFO (DivKid Ochd). Should I get an additional envelope generator (e.g. Erica Synths Black VCA, Doepfer A140, or ALM Pip Slope)? Or maybe a completely different combination? 

If you're wanting keyboard like responses - then an adsr is a good idea - maybe some more research is in order, the erica sysnths black vca is not an envelope generator, it's a consumer of envelopes!!!

I see @Zacksname recommended a matrix mixer - this is an excellent idea for taking simple modulation and making it more complex - get the doepfer - inexpensive, good ergonomics, inverters etc... this will also help with attenuation of modulation sources... often full range modulation is not what you want, attenuation = subtelty

re Maths: fantastic module one of my favourites - really comes alive when you dig in - sownload thte 'maths illustrated supplement' and work your way through it multiple times - concentrating on what, why & how maths is doing what it's doing!!! whilst it's primarily a primer for patch programming (a very west coat concept) maths, the concepts and lessons can be easily extended and applied to the whole of a modular synthesizer

VCA
I know, "You can never have too many VCAs," but how do you choose a good starting point? I've selected a Tangle (4xVCA) and an Optomix (VCAF, if that counts). For output, I’m considering an extra Pico Out. I'm a bit confused in this area (= even more than in the other areas).

optomix good! veils clone really good... continuously variable between linear & exponential response curves (primarily for cv & audio, respectively) etc...

output module: don't buy one unless you need one & if you do try a basic passive attenuator first and a vca second before thirdly succumbing to an output module... unless you desperately must have balanced outputs due to distance or need a headphone output (but better to buy an end of chain mixer with a headphone out in that case)

"you can neverr have too many vcas" - correct, especially quad cascading ones, but the same is almost true about mixers - sub-mixers (preferably with attenuversion and offset - primarily for cv), matrix mixers and a decent end of chain mixer are always good investments

Sequencing / Randomness
With the Moogs and the Keystep I feel there's a lot of sequencing sources available to me already. Therefore, I'm looking for something simple and randomy. I’m considering combining Pamela's PRO Workout with what I already have and maybe a Turing Machine or Wogglebug for some extra uncertainty? I understand they are different beasts. Currently, I'm leaning towards the Wogglebug for a start. But maybe it's dumb to include so many modules by the same maker ... ?

Pam's can do pitched random loops - etc - like a turing machine or wobblebug... except for both of those you'd almost definitely want a quantizer too... which will eat a channel of pam's... start with Pams!

instead of random - consider chaotic instead... triple sloth is great for this...

& don't forget the attenuvertting mixers that you will need to tame the resulting random/chaos either way!

Effects
As I mentioned, I currently use a pedal board for effects, so I’ve included an effects return module but no effects module. Aside from reverb and delay I can't say my music is dependent on many effects. And I've read mixed opinions on effect modules in Eurorack. Optionally I'm considering a Tiptop Audio Z5000 (alternatively an FX Aid XL). Opinions?

FX Aid PRO!!! I have both the xl and the pro... the pro is 10000 times more useable... not only because it has a screen so you can actually see what algo you are using - but it holds almost all the possible algos & includes a basic scope - pesky thing that deaf people use to see what their modulation is doing, instead of just sending it into the pitch input of a vco & using their ears!!!

Utilities
Same as above with some "swiss army knives" like Ornaments & Crime or Disting MK4. They seem useful in that they let you explore stuff you don't have yet as a distinct module. The reason I haven't included them is a) the menu diving and b) that I probably have a lot to play with and to understand already. But maybe I'm totally wrong here and some allrounders might be useful. Happy about suggestions, especially on what other useful stuff is missing.

ah, finally the really important stuff... not the overly complicated digital, menu driven abominations that are O&C & disting, but simple things like sequential switches, logic, clock dividers, mixers, mults, attenuverters etc you need these!!!

take a look at my signature - read it and then spend a considerable time thinking deeply about it and the implications of it for you rack... then think some more... then come back and thank me for distilling such wisdom into a simple formula... I recently had someone say (on another forum) they'd had it tattoed onto their body... I challenged them for pictures, which were not forth coming... I believe I may have called their bluff... but I should get t-shirts made up!!

just kidding about the O&C & disting... well sort of, they are annoying, but they're very useful to have around... especially the disting - which I have - it has to be used wisely though - favourite mode is key and replacing using it's algos with dedicated modules, is a bloody good idea...

Case
In a Rackbrute 6U, this configuration would more or less fit my budget, especially if I can get some modules used. It leaves me with only 50 - 60 ish HP for future expansions and I'm aware that's not much. But I also like it as a compact skiff for gigs and maybe use it in my band. So the reasoning is to add a bigger rack later on and keep this anyway. And I know how that sounds in the context of Eurorack ... but I’ve never been a fan of collecting gear—but let’s revisit that in five years or so. ;)

I've said it before & I'll say it again - TIPTOP MANTIS - best bang for buck starter case there is... combination of price/size/decent power supply & manufacturer reputation there is... it's the sweet spot... some people dislike it's aesthetics - but quite frankly who gives a fuck when it's covered in patch cables and you're rocking out to your bleeps n bloops????????

plus no f'ing rack wart stealing space from important modules and no irrelevant marketing branding shite - if I had one and was playing live I'd have to gaffer tape the back, lest anyone in the audience thought I was playing an arturia synth and not just encasing my modular!!! & the rackbrute is as fugly as I sincerely hope both Uli b-company & the guy who runs Synthrotek's wive's are...

plus it's underpowered if you use too many digital modules... don't do this!!! either of them - seriously leave at least 25-30% headroom on all power rails so as not to oexperience disappointment when your modular won't start up properly - inrush is a thing, believe me... or use too many digital modules... you need utilities too, see both above and below!!!

and... breathe...

hope this helped!!!

"some of the best base-level info to remember can be found in Jim's sigfile" @Lugia

Utility modules are the dull polish that makes the shiny modules actually shine!!!

sound sources < sound modifiers < modulation sources < utilities