Lastly let's say he gets the money and takes care of the taxes and all of that. Now he has to get a code signing cert (not a fast or easy process I would assume) and add that to the list of things he needs to do for each release. We are talking about a non-trivial amount of work over a month or more all so that people will stop bitching about the FREE and OPEN SOURCE product he is producing...
If you find code signing/HTTPS to be so important I suggest you do it yourself, the code is freely available and since it's under an MIT licence you can even SELL access to your code-signed and https-protected putty version. I'm not saying that either of these things are not important (they both are) but let's not jump down the dev's throat because they aren't giving up even more of their time on something they seen no return on.
Putty seeks to perform a security-critical function. It may simply not be realistic to expect that someone can simply step into the market and provide such a tool safely, without putting some effort into building trust with users through, e.g., a code signing certificate. That, after all, is one of the reasons why trust works--it is non-trivial to build.
Again, I don't blame a developer for not doing these things, and I am all for helping developers jump through the hoops they need to jump through, if they are willing.
I say all of that less towards you and more generally in the context of this thread as you did point out "I am all for helping developers jump through the hoops they need to jump through, if they are willing".
But what can we do? I don't think it's realistic to expect anyone to issue code-signing certs for free. Any credible process for issuing the certs, it seems to me, would be too resource intensive for anyone but a charity to do for free.
For projects like Putty it probably won't be a problem to raise money for the cert, if the dev wants to go that route. But I don't know what's to be done about the dev who, understandably, just isn't interested in dealing with all that entails, or projects with smaller followings than Putty.
Do we need to start some sort of organization to help hobbyist and independent devs with this problem? Even if there were a group of people willing to take this on, (I might be), would it be a good idea? Taking on the responsibility of verifying a dev's identity and helping him or her with things like code signing certificates seems like a liability nightmare, for one thing.
The FAQ gives an address for Paypal donations / beer money: http://www.chiark.greenend.org.uk/~sgtatham/putty/faq.html#f...