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You wouldn't be able to sell the 2nd one once you sold the first that maxed the wallet limit.
If there are no other sellers for the same item you will get a notification that it could not be sold because it would exceed your max wallet limit.
https://help.steampowered.com/en/faqs/view/61F0-72B7-9A18-C70B#restrictions
I mean it says this in the FAQ
https://help.steampowered.com/en/faqs/view/61F0-72B7-9A18-C70B#restrictions
No not personally but i read statements by others who it happened to.
But apparently now you cant even list 2 items to sell if their combined price would exeed the wallet limit.
Which is a much more reasonable approach i think, you cant even list over 2000 dollars that way.