Going to start a project in in FreePascal soon because it seems to be the only [not abandonware] compiler for a high level language that still supports targeting 8086.
FWIW OpenWatcom v2 (a fork by one of the original developers who, at least according to the perforce logs, was the most active pre-fork anyway) https://github.com/open-watcom/open-watcom-v2 should also support 8086.
Huh, I'm surprised to find that you're right, unless you count NASM. Randall Hyde last updated HLA in 2015 (and it didn't support the 8086 anyway), WalterBright last updated DMC in 2013, and SDCC doesn't support the 8086. But I remember the 8086 as being a lot of needless effort that we had to cope with because it had a large installed base: near, far, and huge pointers, EMS bank switching, shitty TSRs that would stomp your registers, and so on. MS-DOS made it worse.
Oh I did find this one, albeit I couldnt find much information regarding ot outside of a short reddit thread. Sadly it looks like support expires this year (although I'm sure it will still be stable enough to use in most cases)