That said, I’d love to hear the answer to this question as I paid for a 1.5 license after switching to 2 in good faith that the money would support further development. I’d like to know that the money useful (and that the coffers aren’t running dry).

I just checked when I actually bought a TM license. 
Was surprised to see I paid 50 EUR for it way back in 2009.
TM1 didn't work too well for me, but even so, TM2 easily paid for itself in the first week I started using it. 

Maybe I'll buy another license this week. A single sale of 50 EUR, 7 years ago, doesn't really support the amount of effort Allan puts into developing and supporting TM2

Maybe there should be a way to register the product, and also a gentle reminder that it can be licensed (even if it was just once every few months or something)?

It would serve as a reminder for the people who do want to support it, but perhaps like me, have kinda forgotten how long ago I actually spent anything