Instead of buying more bikes, which claim to be fun, solve problems you actually have. This may involve buying accessories. Make sure you buy the right ones (gloves, use winter boots, good lights, bib layer) not the wrong ones (new bike, new bike, new bike, snacks).
Once I realized that I did not enjoy riding in the winter, I kept doing it. Instead of making it easier and optimizing riding in the winter, I just tried to keep struggling through it. My mental block was that I was saying, "Well, you've ridden before and you've ridden races with this gear, you should be able to ride everyday."
You can obviously ride once or twice in the depths of winter with normal gear. I did. And yes, I did complete a race, which is really just a longer or faster bike ride. But in order to do something, day in and day out, that I think I'm learning, can benefit greatly from extra gear.
To take another example, I can run down the block in jeans and normal shoes, and I can run two miles in that, but should I train for a marathon in that? Well maybe. Can I do that everyday, well maybe, but buying a pair of running shorts and a pair of running shoes would make it much more enjoyable. I might start 'making it easier' through many methods, but it seems common sense to get better shoes.
The problem is what is the problem. And when are those material problems and not just vanity. Are you getting something because you are weak mentally, because they help?
Well what are the reasons to get something?
I think when time and energy are at stake. You need to grow those things, but you also need to be aware when you are taxing them, and then how far you should go with that. When you start asking yourself, who am I doing this for and why am I doing it? The answer should be for me. It should benefit you. Even if you say you are doing it for something greater than you, you should think about how much more beneficial it would be to have you working on it long term vs short term. The bigger picture.
For biking, you can do more, with less gear, if you are in better shape. So get in better shape, mentally and physically. If you were a champion biker on an inferior bike, you would still beat a person in much worse shape. Unless the commitment to that interferes with a greater goal. Then ask yourself, do I still want to accomplish this thing, and if so, how should I do it?
Do I want to bike in the winter? Why? If so, how should I do it? Think about your larger goals and life.