Side Quest 2: The Battle of VM

Background

In the beginning of the HPC era, there was HPC Explorer for WinCE 1 & 2. Then Microsoft's ActiveSync became the dominant synchronization method since WinCE 3. Then after the official end of development of the Handheld PCs, Microsoft pulled out Windows Mobile Device Center (WMDC) for its Pocket PCs and the later Windows Mobile products.

When I started using the Handheld PCs a month ago, I researched the way to have my handhelds communicate with the PC. It turned out that Windows 10 has already dropped its support for its own mobile devices for good. Not even WMDC is working without certain tweaking.

To get WMDC working, follow the instructions in the first post here: https://www.hpcfactor.com/forums/forums/thread-view.asp?tid=18889&posts=3&start=1

However, there is a big caveat. When using WMDC to synchronize the old HPCs with Win10, certain programs, particularly those which have their own desktop companion programs like HPC Notes Professional, will fail to install and synchronize with the devices simply because those old programs were coded to require ActiveSync specifically when Windows Mobile or WMDC was not a thing yet.

So far so good, but after a couple of weeks, another forced update of Windows 10 killed my WMDC set up. I searched all over the web and found no solutions to get ActiveSync back to work in Win10. 

And then it dawned to me that if I couldn't get ActiveSync to work, then how about getting another OS to do that?

The Battle of VM

I have chosen Oracle VirtualBox (free) to set up different OSes to facilitate a better handheld experience. Initially I resist the idea of VM as it sounds like too much work and feels cumbersome (i.e. running another OS within the main system). The upshot here is a VM can work like a semi-sandbox and is highly portable, i.e. the same virtual machine .vdi file in principle can be used on any machines running VirtualBox. No need for a separate old PC to take care of the old buddies. Plus having a dedicated environment purely for my handhelds and without letting old stuff mess with the host Win10 also feels so good.

Here are the AARs:

Windows 98 (SE): In principle it should be the ideal choice. Being able to use DOS natively is a huge advantage for retro users like me. However, support for Win98 is rather disappointing. Considerable tweakings are in order to get SMB1 to work. Display driver is a nightmare (stuck with VGA mode in 16 colors). USB support is flaky. Crashing is frequent and sometimes can be fatal. Frequent DLL errors and BSOD lead to reinstalling the whole system and wasting the whole effort.

Windows XP: Too modern and too bloated to my taste. I want something more compact and lightweight to fulfill my exact purpose (i.e. being a kinda central hub for my handhelds and nothing more). And I have to admit that I've become paranoid about its security holes as XP seems to be the most targeted version.

Linux: Support for ActiveSync seems rather obscure. Windows programs need to run in Wine but there is no guarantee they can actually work. Not an ideal solution either.

ReactOS: Feels really like between Windows 2000/XP and Linux. USB support is barebone. Runs pretty fast and smoothly, though. But ActiveSync fails to install, which is a show stopper.

Windows 2000 (SP4): My choice for now after so many failed experiments. My VM uses a 8GB of HDD space, 2GB RAM, 128MB video RAM, plus Virtual Box's own Guest Additions. 

File Sharing, Clipboard Sharing, Drag & Drop, Mouse Integration, etc. all work right away without extra fiddling. 

Everything runs blazingly fast, to be honest much smoother than my Win10 host. 

The biggest pro is the speed of synchronization (both ActiveSync and Palm HotSync) with my Jornada and Alphasmart Dana via USB are MUCH faster than under Win10. Compared with Win98, Win2000 is far more stable and "handhelds friendly". In addition I turn off the VM's internet access and can only access the host Win10 via one specific folder.