So you don't have 320k drives? Good. That clears up that mess 😉 You might want to come and visit over at vcf. Pre pentiums are the norm over there and the members don't bite. They might even be able to help with your 486 mobo issue if it's fixable. Might even be some one local to you who can help out.

I'd say depends on what makes your life hell and what you enjoy.
I'm dreading needing to recap my later motherboards although I know I'm on borrowed time.
My 486 DX4 really didn't want to play with CF cards at first, few days of trial and error (which I enjoyed the challenge) now it runs like a dream
My 486 DX2 on the other hand is being very well behaved and offering no challenges at all. A little boring in the end

Also comes down to the hardware. The DX2 is the first time I've used a Gotek floppy drive from the very start, installing Dos/Win 3x onto a basic IDE drive and getting networking up on my 100% NE2000 compatible NIC is no drama at all. No disks or CD's that cant be read. USB stick till the networks up then everything else over the network and everything has well behaved drivers.

This where OEMs are great. Usually very well documented. I like 286, 386 and 486 platforms: not that many hardware options. I have not used / owned a 5.25" FDD for a year+ and I like it that way. Transferring data with a LapLink cable and/or CDs works great for me. I rarely put stuff on diskettes anymore. Only when it is something small and/or temporary. 🤣

HDDs work great as long as you punch in all the right parameters normally.

I don't see that there is any inherent problem with 386 vs 486 vs Pentium etc, providing you have the mobo directions. I have two 386s. One is from 1989, @ 20 Mhz and has 2 MB of Ram. It seems very ancient compared to my other 386 which is an AMD 386 @ 40 Mhz from 1993 and has 32 MB of RAM. The older one which is a dual booting DOS/MOS machine has lots of jumpers, but the instructions are all very clear on what to do with them. The newer one is running Windows 3.11 with networking. So that machine is virtually modern. The older 386 does not have networking so I DO rely on the floppys to move a file or two back and forth. However, it has a 1.44 MB boot drive and a 1.2 MB secondary. I can't imagine a reason to retain an old 360k drive, unless it is for strict originality in a "show computer" or something like that. I also upgraded the old 386 from the original MFM hdd which was RLL formatted, with a smart IDE controller capable of handling a couple of 40 MB hdds with its own BIOS. That really helped make that computer easier to maintain.

I also have a 486 @ 66 Mhz and 128 MB of RAM. That one is running Windows 95b and is on the network. It isn't hard to work on either since I have the original Gateway instructions. Actually the plug-n-play is not THAT dependable, and you are still required to set some IRQs and Addresses when it comes right down to it.

Of the three, I enjoy the newer 386 the most. It runs Windows, has networking, and is still very DOS oriented, booting into DOS 5.0 first. To me it is like the best of both worlds. 😎