Feeling a bit more confidence in producing (though I'm just starting out) a project. One thing I'm looking for which feels a bit beyond my spriting ability is ... I call them talking portraits? Can't quite place a solid example of them, here is some screenshots of some games that might give an idea.

Solar Winds - Small boxes with a characters portrait, simply enough ... but with mouth and eye animations that go along with dialogue.

Z - Your robot units in the top right corner had similiar.

Battle Isles 2 - The dialogues you get coming up here and there, the portrait box is bigger, but it had (I think at least) very simple mouth and eye movements to an otherwise still portrait.

The following are some more high-end examples - probably not the kind of art I'd be able to afford, but if the above examples don't click these might.

Tie Fighter

Dune

Dune II

In a way I'd quite like a 'modular' portrait, where you start with a base face and it can have different hair/clothes/eye colour randomized ontop of it. A bit like Pioneer or Elite I think? The above examples are an art style I'd quite like to emulate for my project. The portraits have minimum expression and animation ... I imagine you could almost layer the mouth and eyes on top of the face and have it play through a series of frames to animate the talking.

What are my chances of finding some one who would do this kind of art? Is there a good place to find artists of the more retro(?) style of the above?

What sort of details can you offer? I've done talking head portraits before, though they were more simply shaded, more of a cartoon than a painting. (Those are simpler, incidentally, since the shading is simplified and less prone to mistakes.) I worked with these guys for about 7 years, and about half the games had that sort of talking portrait/sprite tech involved for storyline moments.

http://www.ninjabee.com/games/

Do you have characters designed or are you looking for a character designer also? How many do you need, and how many phonemes/expressions? What sort of deadlines do you have, and what sort of budget are you working with?

If I can't wrangle the time to work on it, I also know other artists who might be open to some freelancing.

Sorry, should of mentioned this was more a query of interest/likelyhood? than anything solid at this stage.

As for the scope ... lets say 8 generic bald human faces (younger, older, different ethnicities) which could than be customized with 'hair pieces' 'hats' 'shirt collars' 'facial hair'. Think a sort of Mr Potato head deal ... as for animation and expression, all I'm really after is some mouth opening and closing in a talking like fashion (game will be text based) and some eye movement from side to side with perhaps the occasional blink. Definitely not really going for a colourful cartoon style though.

I'll be honest, I have no idea about budget, most of the project was going to be homebrew ... what sort of cost am I looking at for this kind of thing?

It's going to vary wildly by how much a freelancer will charge and how fast they work. Also, if you have a style guide you're aiming for and want them to conform to, or if you are OK with them deciding on the style. (Those images you have posted are a good place to start, of course.) Graphic size will matter a little, but the real key will be the amount of work that you want to go into them.

A cartoony style (even if it's subdued in color) will usually be faster (mostly a line drawing with minimal shading), especially compared to those Sierra-style or Star Wars-style large "painted" portraits. Cartoony can mean something as clean and appealing as The Last Airbender, or as flat and goofy as Scooby Doo.

You'll want to nail down how many attachments you want, too, and how those would change with expressions, if at all.

It's hard to estimate without more details, but those are some things to decide on, perhaps.