Okay, so I gave up waiting for Twonky support to respond and just went ahead and tried the upgrade.
Here's my findings...
The HP version of 4.4.4 seems to be a 'special' version. It doesn't have a license key and its installation/license is controlled by the installer msi, i.e. if it's not a HP MediaSmart, it won't install. Therefore, you'll need a new key for upgrading to any other version; luckily I had one from my previous (non-WHS) server so this wasn't a problem.
Twonky 4.4.11 does play semi-nicely with the HP Add-In but requires a manual selective install to make it work (i.e. installing on a doner machine and then copying the required files).
So far the only thing I found that that doesn't seem to work after the upgrade is the list of "Enabled Media Receivers" on the Add-In's tab remains blank. With 4.4.11 this list is maintained in a new file so the Add-In is now looking for them in the wrong place.
For me this has been a successful upgrade because I can now stream Matroska files, and during the process I decided to enable the standard Twonky config web pages so can now fully administer it from any PC... which has kind of made the Add-In redundant anyway.
FYI, here's what's different between 4.4.4 and 4.4.11...
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What's new in Version 4.4.11
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Bug fixes:
- inotify follows symbolic links, if followlinks=1
What's new in Version 4.4.10
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Bug fixes:
- devices TEAC WAP-4500 and WAP-8500 supported
- no timebased seek for WMVMED_BASE
- cgi-jpegscale improved
- fixed handling of bad inotify events
What's new in Version 4.4.9
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Bug fixes:
- no timebased seek for WMVMED_BASE
- cgi-jpegscale improved
- fixed handling of bad inotify events
- fixed Itunes import plugin
- fixed client database not detecting some clients
What's new in Version 4.4.8
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Bug fixes:
- fixed broken utf8 support in ini file parser
- merged the two PS3 client adaptation settings into one
What's new in Version 4.4.7
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Bug fixes:
- fixed DLNA_QoS for non-DLNA-1.5 clients
- now accepts also folder.jpg (all lower case)
What's new in Version 4.4.6
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Bug fixes:
- fixed PS3 recognition that was broken for >= firmware 2.4
- fixed general transcoding for specific conditions
- fixed inotify on toplevel of content directory
What's new in Version 4.4.5
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Bug fixes:
- set pthread stacksize to a reasonable value
- fixed numeric genres which are not mappable to id3v1
- fixed xml tags and entities in language files
- fixed SSDP messages for multihomed server
- fixed different handling of AVI for PS3