Hello again, slewis36. You ask good questions. Want to say that I understand where you're coming from, I think. I was scraping by on just a VA pension, while my SS disability was taking forever to be decided. Now that I in fact get SS also, I have more discretionary money.
I think many of the answers you've received here are excellent. But, I'd like to suggest a $15-$20 side jaunt on your trip towards custom ownership. You might be able to find it at the local library. Anyhow, try to get your hands on a copy of Ed Fowler's book "Knife Talk."
Ed is a very highly rated bladesmith, who has a Master Smith rating from the American Bladesmith Society. He also is an uncommon wordsmith. He has a down-home style that many relate to very positively.
Ed is a philosopher of many kinds, including knives. He is on a lifetime quest to reach the holy grail of knifedom, the perfect forged steel. Much of his writing, and all his knifemaking is directed towards "high performance" knives. Reading his book drastically changed my perspective on knives in general, and especially custom knives. Since reading his book, I have bought a Sebenza, in many people's minds the top end of manufactured knives. I also have ordered my first custom knife. It makes perfect sense to me. I envy your having a bride who is supportive. I can't even talk about knives at all.
I'd also like to suggest that you maybe spend some time reading the Shop Talk forum, if you haven't been already. Doing so, you get an idea of all that knifemakers must know and do to create good knives. You also are likely to be flabbergasted about how helpful knife makers are to each other. I am constantly astounded by that.
One more suggestion, that sort of follows one suggestion already made. If you can get your hands on the last year or so's issues of Blade, look for the article on the makers with knives for sale under $100. You might be surprised what you can get if you shop carefully. Maybe in the same issue, special mention was made in a review of the Guild show, or some big show in New Orleans, about how many knives were available around $100 at that show.
Good luck!