Initial success! After some configuration and compilation trial and error I think I've got the magic sauce now to get ioftpd to compile.
1) I've upgraded tcl to latest stable and php to latest of v4 lineage (I don't use it, so not sure what might break script wise if upgraded to v5+).
2) I can login using SSL, and transfer files over SSL.
3) I've got tcl and exec scripts working (don't use php but it probably works too). Most notably ioGUI using itcl. I might be mistaken but I don't think anyone has made this much progress in a long long LONG time. I don't remember anyone saying that 5.8.6+ could survive running the tcl version of ioGUI which is what I'm using. So I think this is looking good.
4) Of course just when I thought all was good "site shutdown" appears to have some bugs in it that for some reason are surfacing now. Examine the logfile after you issue a site shutdown and you don't get a user logout message. You should though, that message is in fact stuck trying to get written to the logfile and is crashing ioftpd. I've already fixed 2-3 bugs trying to find what was going on and now I sorta think I have an idea but not sure what's the best solution as I'm not really very familiar with the job system yet.
Anyway, just wanted to report that it has life. Hopefully soon I'll put out a new version
Doh! I think I just cursed myself...