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Mostly because I'm a Mac bigot, but also because there are some users of launchd on other systems, I will add support for this in 1.6 in the form of configure.launchd. I have not yet determined specifics. For now, OS X Tiger users probably should use Demonic and roll a .plist for autostarting on bootup. Launchd Editor will be the best help here.
1.6 will have a configure.stunnel to allow SSL. Note that there is nothing precluding using stunnel for this purpose already and it will work largely as-is (probably best to use configure.inetd, or allow stunnel to proxy the port; note that transparent mode is currently required); this would just make it officially supported and more convenient.
There are now several requests for this and it will be supported, but I am waiting for stabilization with Perl's IPv6 support before I do so.
Executables that die under HTTPerl in 1.4 and up and return control to the default handlers generate two log entries, one with a return code of 100 and another with the error code (usually 500). Although annoying, the code to defeat this on my inhouse test version turned out to be involved and unreliable, and for this reason I have left the double logging issue alone as a "feature to flag bad executables." It does not affect versions prior to 1.4.
Yes, I know this continues to be an issue. There seems to be some problem with the Classic Mac MacPerl site, and it doesn't seem to have been updated in some time. Now that I have Virtual PC on my dual G4, though, an ActiveState port may become available. I am waiting for patches from one user who hacked up inetd-based HTTPi to work in this environment. Still working on it.