I've only messed with the standard 4.2.7 version of winboard, but yes, that version works well in wine. Although it works with builtin riched20, I recommend using a native riched20 if you use it as an ICS client.
H.G.Muller wrote:I have little Linux experience, and none with Wine at all, but I am asking this on behalf of a non-Windows user that wants to observe first hand what exactly the differences in graphics capablities are between WinBoard and XBoard.
To be sure you get an accurate depiction of winboard, you can always run it in a VM. Virtualbox even has a seamless mode where windows and native linux apps coexist on the same desktop.
H.G.Muller wrote:In particular, would it still be possible to use true-type fonts for piece rendering, and bitmap background textures for the board?
I would think so. But to be sure, it must be tried.