Kurt,
I am the principal system developer at this time. For the last two years, I have been the only person doing system development, and I work as a volunteer. FTH is independently developed and maintained strictly with volunteer labor (all volunteers are also Toastmasters) and we do not have any budget to hire people or farm out development work. We do have another person that has recently volunteered to assist with development, but since the system is very large and involved, it is going to take a bit to get them up to speed.
This https improvement is on my to-do list--I have not forgotten it. However, the main problem that I have to find a way to resolve is that while we can switch to using https on the main pages, the website spawns many other pages (e.g. reports) that also need to get addressed. It is *not* as simple as you may think. This is a system wide, global change that has wide ranging impacts.
So... while I actually did try to make the switch a few months ago, we ran into issues (w/ reports) that indicated that there was a good bit more work involved in this than I originally thought.

We also have to switch from https to http for clubs with a custom domain since our security certificate only addresses the toastmastersclubs.org domain.
Unfortunately, this is the fundamental conundrum with FTH being used for corporate clubs. We really do not have the means to quickly make changes that corporate clubs may be expecting. Also, while we certainly are interested in good security, if you look hard enough, you can probably find vulnerabilities. All I can promise is that we (me) will try to do the best we can to make improvements as my available spare time permits.