Express 3.5" barrel on a 2 3/4" Wingmaster Receiver?

In my experience with a similar Wingmaster, the express barrels fit fine. Stick with the shorter shells regardless what the barrel is cut for. The receiver could shoot the longer shell but likely to have feeding amd extracting issues. It used to be a cottage industry modifying older 2-3/4" receivers to shoot 3" shells reliably with 3" barrels. Seem to recall it didn't always come out 100% reliable.

Standard express barrels are 3". Supermag express are 3 1/2". I could be wrong but I think the Supermag barrels don't fit standard frames.

this guy might have done one or two as a Remington authorized guy (I believe...). Give him a call... that's what I'd do first thing....
https://www.aiptactical.com/

I had a 3 1/2" gun briefly a few years ago. I'm 90% sure they will interchange as long as you use the right ammo. But it has been long enough that I'm not 100% certain. I realize that doesn't help, but I'd continue doing the research instead of just giving up.

I know the older wingmaster barrels are thinner in overall contour, will there be any fitment issues with a modern Express barrel

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That I can answer. You have to 1st define older. If the gun is old enough to have fixed chokes the barrels are thinner. When Remington initially went to screw in chokes they had to make barrels thicker to be threaded, but people complained about the weight. So they developed a "Light Contour" barrel used for a while. Until they had issues with barrels splitting along with a Class action Lawsuit over diminished value. I'm fairly certain no one was ever hurt by this. But they went back to thicker barrels. Not just on the Express. It's just that the Express barrels were never "Light Contour". At any rate in some cases a little wood might need to be removed from the forend to fit a thicker barrel. Maybe not, but it isn't a big deal.

I have a very old wingmaster and a slightly newer Express Mag. and have bought assorted barrels for both and they interchange easily with no modification. I do highlight label my 2 3/4" barrels when I put them on my Express Mag. frame.

Happened to get this in a sale email today. Not sure if you got the express barrel yet, or what length you were looking for. If a shorter barrel with chokes is of interest, certainly not a bad choice.

https://www.cdnnsports.com/remington-870-12ga-18-5-custom-barrel-target-sport.html?trk_msg=TP8U5DAUS68KB6U0BLIAVUSR2K&trk_contact=VOB84UBTRGQF6PLAEGO254TOPO&trk_sid=R4Q0REVOSLE6LPHGQJCDOL50H8&utm_source=listrak&utm_medium=email&utm_term=https://www.cdnnsports.com/remington-870-12ga-18-5-custom-barrel-target-sport.html&utm_campaign=CDNN+Special+7-19#.XTHnJ1NOk0N

* edit - they also have a full length 28" with choketubes for $10 more