https://bugs.winehq.org/show_bug.cgi?id=40990
--- Comment #15 from Alex S iwtcex@gmail.com --- (In reply to lehmannwer from comment #14)
I have tried previous versions of wine-devel, but they seem to be for 64-bit only, with only a "wine64", but no "wine"-executable. Is that still the case?
On an amd64 FreeBSD system wine (-devel, -staging) package provides a 64-bit build of wine, the same package for a i386 system contains a 32-bit wine build. Packages with the "i386-" prefix are 32-bit wine builds repackaged for a amd64 FreeBSD system. I.g., i386-wine-devel is a wine-devel built for a i386 system with some appropriate changes applied (/usr/local/lib -> /usr/local/lib32, etc).
So I would not be able to play 32-bit games with that?
Generally, yes. Wine FAQ (https://wiki.winehq.org/FAQ#Is_there_a_64_bit_Wine.3F) says you can do this provided you have "32 bit libraries" installed, but it doesn't elaborate on that. It certainly isn't out-of-the-box experience.
But I still have a question regarding wine-2.3, where it is said that the issue is fixed: For now, there is only wine-devel-2.3 and wine-staging-2.3, but no i386-wine-2.3.
First, you can build the latest wine yourself with instructions at https://wiki.freebsd.org/i386-Wine#Building. Just make sure to skip "make buildword", "make installword" and "make distribution" steps: fetch https://download.freebsd.org/ftp/releases/i386/11.0-RELEASE/base.txz instead, verify it against the checksum in /usr/ports/misc/freebsd-release-manifests/files/MANIFESTS/i386-i386-11.0-RELEASE and extract the contents to /compat/i386. It is also a good idea to install build dependencies with pkg, otherwise compiling them from ports would take quite a while (see http://serverfault.com/questions/334934/freebsd-ports-how-can-i-see-all-depe...).
As for your question: curiously enough, even so the packages in the official FreeBSD repo are built with Poudriere, this particular package isn't being built through the "WINE_CROSS_BUILD" procedure described in the wiki (which goes through i386-wine-devel/Makefile.i386). Note that each architecture requires it's own separate Poudriere controlled jail. Building this port actually involves maintainer (manually?) copying regular wine-devel package produced by the i386 jail to local distfiles (yes, that's a thing; basically, a place on the FreeBSD project servers from where it could be refetched by the port's build script) and then updating PORTVERSION in i386-wine-devel/Makefile.inc (https://svnweb.freebsd.org/ports/head/emulators/i386-wine-devel/Makefile.inc...). After that it would be repackaged by the amd64 Poudriere jail. This, naturally, leads to i386-wine-devel always lagging behind wine-devel.
It's a good question in itself why things are done that way (as opposed to WINE_CROSS_BUILD). Most likely there is no support for publishing an amd64 package from the i386 jail, but I have no idea really.
Sorry if that wasn't clear: I'm not a native english speaker, I'm lousy at explanations and this a bit complicated topic to boot. Try asking on the FreeBSD forums if you need help with anything above.