CF - Probably great in windows, but would it be visible in DOS?

Possibly. You need drivers but generic ones should work.

Wi-Fi - Would WPA2 be supported?

I doubt it.

10/100 - Might be a good bet AFAIK

certainly

USB 2.0 - Are there mass storage drivers in Win98/is this even worth it?

PCMCIA is too slow for USB 2, you would have to settle for USB 1.1

Thanks for the reply, good to have a second brain, 🤣. Guess I'll start hunting for a wired LAN card first and maybe a CF reader second. Much appreciated!

I've used both CF PCMCIA adapters and LAN card in similar era laptops - A Thinkpad 560X with as 200MHz Pentium and a Toshiba T2450CT with a 75MHz 486DX4. In both cases I could not get either option working in pure DOS - I could not find working drivers. They both worked perfectly out of the box under Win98 - the Win98 install CD includes generic drivers for the CF card adapter (which is just a passive adapter) and the Xircom LAN card.

The 560X was my daily driver for a while so it spent most of it's time running Win98. The Toshiba with it's 486 and 16MB RAM was surprising responsive in Win98 (I did use 98lite to strip out the IE shell) - I usually booted in Win98, copied the files across the network and then rebooted into DOS to actually run games. A Win98 install can be stripped down to under 100MB, so even with an 800MB hard disk I wasn't too concerned about the space it took up.

I did use an Orinoco WiFi card in the 560X under Win98, but only WEP was supported and the drivers were unstable.

I do this all the time - if it has a USB port from that era, it's probably a USB 1.0 or 1.1 port. Even if it was a USB 2.0 port, they're all backward compatible... you'll have no issues loading drivers in DOS or Windows 98 for flash drives.

Here's what I would do:

1. Make a DOS 7.1 boot floppy from the CDU images available in various places (search "CDU DOS 7.10" or "China DOS Union"). This floppy will have USB mass storage drivers on it.
2. Use the floppy first to format the drive and copy the basic system files to it (FORMAT C: and SYS A: C:)
3. Then reboot with a USB flash drive in the port, containing the files you need, select floppy at bootup and select the USB support option. Then copy your files using XCOPY and away you go...

The files on your flash drive could include a folder called WIN98SE with the contents of the Windows 98 SE CD. If you copy this to the root of your drive it makes things way easier and you never need a CD drive at all.

You'll also want to copy over NUSB so you can install USB drivers in Windows 98 once it's installed, and copy the rest of your files/drivers that way.

Alas, no USB ports... To make matters worse, I just discovered the floppy drive in the laptop is non-functional! 😢
I shall not be deterred, I have a eide to USB adapter that I "borrowed" from work and a 30Gb HDD, it's acting a little funny under windows, but seems to work better in Linux. I am hoping the fact that it is under the 32Gb limit of FAT32/Win98SE will be a good fit for this system. We shall see.

I'm going to try a clean install of Win98SE inside a VM, grab an image of that, and then apply/copy it to the donor drive. Sounds crazy, but it might actually work.

I also ordered a couple of items to help me along, should be here in a couple of days:
- PCMCIA-Ethernet-Lan-Adapter-DFE-690TXD
- Cisco Aironet PCMCIA 350 Wireless LAN Adapter AIR-PCM352 PC-Card
They were cheap on EBay and I may need them for future endeavors.
I also located a HP floppy drive with a LPT connector, but that's not working either even with bi-directional/EPP/ECP turned on.

You’d have to copy the image byte by byte somehow, in order to preserve the master boot record. I would boot another machine with the DOS 7.10 floppy somehow, or the CD (yes, CDU made a CD as well), or even a bootable USB, with the USB to IDE adapter connected, and partition and format the drive, and copy the system files with SYS A: C:. Then copy whatever else to the drive, like the contents of the Windows 98 CD, using Linux.

Understood, I may try that if the VM thing doesn't work. I've done it before by creating a VM and then making an image by booting Clonezilla ISO and saving the image to a mounted share or USB device. Once that is obtained, I can restore VIA USB on the host computer and then plug that drive in. I want to preserve the original HDD because it has some interesting stuff and probably drivers that I am going to need. When I tried the USB adapter in Windows, it wouldn't read and started making a loud clacking sound that scared the bezeezus outta me! I immediately put it back in the laptop and thank God it still boots. The new replacement drive had no issues partitioning and formatting to FAT32 in GParted. I'll try to preserve the OEM drive using Linux tonight tonight and post results after work.

Thanks for the suggestions, this is truly a "pick yourself up by your bootstraps" problem!

Okay, I just found a USB floppy drive at work and it tested good on my work computer. I'll be sure to take that home with me tonight.