What should I get???

You've got the sports covered with the 70-200. On DX a 50mm will do the portrait thing. Adding a 85mm will give you some benefit in Bokeh, but it's usefulness depends on what type of portraiture you are into. Head only, full body or torso? And of course the distance to your subject.
I'd consider the 85 1.4 for it has a creamier bokeh than the 1.8.
Choosing between a D300s and a D90 is quite easy for me. The D90 would make a great back up body or good looking paperweight.

Not to be snide or obnoxious, but if you have to ask....
What does your current kit limit you from doing? If you did more landscape, I could see needing something wider in the lens line. IF it were me, I'd keep the D300s and dump the D90 and buy the 12-24 f4, or just buy the 12-24 for the d90. Personally, I like the faster shutter speed, 100% viewfinder and fps of the D300s. But that is me.

I think the 85mm f1.8 would fit in there nicely for portraits along with the 50mm. It does not hurt to have two camera's and sometimes the lighter weight of the D90 will be just the ticket.

Are you saying you are returning the D300s? It is in a different league than the D90; certainly not a replica of. Not saying the D90 isn't a good camera but the D300s is a superior camera. In terms of lenses, do you find yourself wanting to shoot @ 85mm with a wider aperture? You have the FL covered @ f/2.8 with the 70-200. I would probably look at the Nikon 17-55 or the Tamron 17-50.

With a 70-200 I`d not be interested on a 85mm lens... the prime is more than one stop faster but, how many pics will you take at f1.8 and not at f2.8? If you need a lighter (consumer) lens, then it`s ok.
Looking at your gear, I`d miss something to shoot indoors and for all-round use.., I agree with Douglas about the 12-24. Just add a 35/1.8AFS for casual shooting and that`s all.

Exactly what type of sports do you shoot? AF on the D300s is considerably better than what is on the D90, but only you can tell whether that will make a difference for you.

Concerning lenses, do you have any wide angle? If not, that seems to be an obvious hole, especially if you are now into landscape work.

Andrew, the image quality of the D90 may be the same as the D300s, but the D300s does have more going for it. the 51 point AF would actually help you in sports shots. the faster frames per would help in sports shots as well. I own a D90 and love it - but I do not shoot sports. I also would not buy a 85mm since you already have the 70-200 2.8. I probably shoot 1/3 of my portraits with it, the rest goes to the 50mm. if you do not shoot landscapes a wide angle will see limited use IMO. honestly, If I was in your shoes I would keep both cameras. have the 50mm dang near permanently attached to the D90 and the 70-200 attached to the D300. The do D90 could go everywhere with you and the D300s could be used for sports jobs and photoshoots. just my 2 cents

For sports, you will miss the D300's AF system which is the same as the D3.

I have to agree with so many here. You're going to get rid of the D300s & you shoot sports??? That's an interesting way to go about things. ;-) The D90 can't hold a candle to the D300s for sports.
Ah well to each their own.
As far as I'm concerned, if you have the 70-200VR - why buy a 85mm?
Personally I'd spend the money on a wide angle & hold on to that D300s & keep the D90 as a backup or sell it off for yet another lens...
But that's just me....

Why would you not thinking about 17-55 2.8 ? Excellent lens for DX.

If you are serious about sports, then D300s makes sense. The D300s should be about $1,500 and this leaves you with just $300. You do not have any wide angle or normal zoom. The popular Tokina 12-24/4 or the Tamrom 17-50/2.8 can be found for around $4-500. I have the 85/1.8 b/c I don't have the 70-200, which is way too big and heavy for me. I use the 85/1.8 for portrait and for traveling as it is so much lighter than the big glass. I rarely use the 85 at 1.8 b/c the shallow DOF makes it difficult to get everything needed to be in focus in focus so I end up using it at 2.8 most of the time. Since you already have the 70-200/2.8, you should spend it on other things.

Keep that D300s!!!

And don't get the 85mm 1.8.
Get a 50mm 1.4. The old one is as sharp as the new one, just quicker in focus and cheaper as a second hand one.

For the portraits:-

85/1.8 afd - $425 or 50/1.4 afd - $325
Elinchrom D-lite4 strobe head set with softboxes and stands - circa $750 from Calumet
Pocket Wizards - $350, flash lightmeter - $185 and grey muslin background - say $90

There, that's $1800 easily spent.....

The strobes will cover your model, the PWs are essential if you don't want to walk thru your cables dragging it all to the ground, and the grey sheet can be anything from black to white with colours in between (with the correct lighting/apertures and gels).
Reflectors and all the gobos will keep your good wife spending for years! Tell her the better you get the better she'll look :) This set will also serve you well for all manner of macros and product work too.

If you can live with the pc cable and leave the PWs then get another strobe head for the background illumination.

Another vote to keep the 300. But, you don't have anything longer than 200mm. You don't have a macro. You don't have a F1.4. I think most shooters would do as Kevin recommends. After all, all of your lenses are teles.

Thanks for the responses! I do shoot sports and never had a problem with my d90 or complaints. Are you telling me I could do BETTER with the d300s? I haven't taken it out of the box yet.
I was thinking about the 85mm 1.4 for the creamy bokeh. Plus, not everyone gets to say creamy bokeh everyday; such a cool term.
Landscapes is more of a hobby; sports and portraits are what I tend to drift to more often.

If he does not shoot macro why would he need to buy one? I am guessing the $1800 is based on if he takes the D300s back (which if your shooting sports is a mistake IMO). you have decent lenses for Portrait work in the 50mm and the 70-300 is great for 1/4 and tight head shots (depending on how far back or forward you are) and the only thing you may be lacking for sports is more reach. if your shooting night games this will not help but for day stuff a 1.4 telecon would give you that reach coupled with the 70-200. Not the best solution, but the most economical.

I meant to say 70-200. but yes Andrew the D300s will shoot better sports than the D90. The 51 point Af will help during tracking and panning, the D300s also shoots upto 7fps compared to the D90's 4.5fps. I hear that it is 8.5fps with a grip (I have not tested this).
Do not get me wrong, I love my D90 and probably will not switch to another DX format in my next purchase. I am aiming for the D700 (D700s I am sure in 2 years). but for a cropped frame camera, shooting sports, the D300s does beat the D90. Since the idea is to be able to track the movement, and capture the right action, the D300s is just plain faster.
I still say the 85mm 1.4 would be a waste of money for someone that has not only the 50mm but the 70-200.

You guys rock, thanks. Now my wife won't be so mad at me when I tell her that I'm not taking the camera back....

Plus, not everyone gets to say creamy bokeh everyday; such a cool term.

I use it as a mantra and say it several times per day.