Years ago I used to have some fun selling higher end production knives. Mostly slipjoints. I collected them mainly so it was not about making money, it was just about going to shows and meeting people. Sometimes I actually did make some money and brought more knives.
Back then the Blade Show was in two different exhibition rooms each year. One room for production and another one for Custom knives.
I made the "mistake" of wandering into that big room full of custom makers and have not come back out since.
As far as production VS custom knives. I still love them both over 20 years later, but I enjoy the people involved even more.
I now do most of my buying by ordering knives from makers, buying the occasional factory knife that says take me home and the Blade Show. I have already started saving for next year. The hobby for me has always been enjoyable, I think the key to that are some wise words from my brother.
Owning your first custom is very rewarding but as you say in the OP it must be tempered with the responsible and judicious use of funds for meeting all family obligations and commitments first. Maintaining that hierarchy is paramount. I think you've got your priorities in order (imho) and I hope you'll find yourself the owner of some great custom knives down the road.
I remember the that feeling when I purchased my first two custom knives over 20 years ago. It was a little odd.
I also remember the feeling when I sold those two knives (a forged bowie by Howard Clark and a pretty fancied up folder by Mel Pardue). They actually turned out to be excellent investments. I turned them in order to buy a few custom slipjoints for the first time.
Last year I decided to go into business. Took a look around at what I could do to handle the start up costs and realized I had a good bit of cash tied up in knives. More so than a sane person should have, but I was happy with them. I sold about 1/3 of my collection. In one way I am glad since it helped me gain some independence after 30+ years of writing software for companies. In hindsight, I wish I did not have to sell them, but it was better than going into debt to start things up. They turned out to be excellent investments, but I wish I could have kept them.