Hi Anthony
Firstly, a huge THANK YOU 
- for your great support to this community over the years (those who remember, RevGenetics was also a brilliant partner in making our crowdsourced supplement Vimmortal available) -- but also for your incredible patience and perseverance. The video was really helpful in understanding the issue.
I spend quite a few hours trawling through legacy code. The ad booking is tied up with the general payment system and I'm always weary of breaking something or compromising security. Frustratingly, all particularly relevant bits seem to have been encrypted by the developers (apparently a third party provider to Invision who have long since moved on) and I can't even get to the part of the scrip that generates the confusion - not even on the display ('skin') which is silly and quite unusual for our software. Having said that, I am not a programmer by any stretch and it is also entirely possible that have missed something obvious!
Firstly, (and this may be why the problem has not been noticed): there is a workaround, but it's a bit stupid:
it works IF you
1) link to a http not an https page AND 2) upload your ad image manually, rather than link to it AND 3) the image is not too large
Then, there is another problem. This one we have known about for a while, but also can't seem to fix it properly:
If two people book the same slot, the system doesn't cope well (This happened for you vs TheCarbonGroup ("Alive by Nature"))
Now, of course this state of affairs is really not great. You are a saint for persisting but how many potential supporters have just walked away in frustration?
Among the possible solutions:
1) We abandon our dream of having a fully automated system. Sponsors work out a deal and we display the ads manually. This is always the fall-back option and one I would suggest for you at this point. Talk to Mind and we'll make it happen. The downside to this is that it eats into volunteer time, is more prone to human error and while the personal communication can be very nice and helpful it could also introduce more of a relationship bias that we'd like to steer clear of with a non-profit like LongeCity.
2) We abandon the bookable ads system and run ads via google or some other platform. Unfortunately, as you may have seen in the Members section a few years ago Google seemed to have changed their algorithm in a way that hurt us severely. Going through Google is likely to be less effective for both sides. Alternative ad vendors are another issue: we tried that rou8te a few years ago and the results were not that great.
3) We try to hire someone to fix the IT interface. Unfortunately this would not be a casual undertaking. Again, since this is payment related we'd need to make sure this was done properly and at this stage I'm unsure whether we can fix the problem in a manner that costs the org less that we'd be taking back in for the community even in the medium-to-long term.
We'll be having a chat about these and other options internally, but I'd invite you or anyone interested to chime in here as well.
Again, thanks for pointing this out and for your goodwill towards this community.
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