Don't know if this will help, but here's a story. It happens to be true, No internet exaggeration. I know it is true, because it is my story.
I'd been following benchrest since my late teens. I'd shot NRA 4-position (rimfire) as a junior, so was interested in accurate rifles. Probably wore out a copy of Warren Page's The Accurate Rifle before ever getting to a benchrest match. In fact, I didn't get to a match until I was almost 40, just starting a new business, working 90-100 hours a week and taking minimum wage as a salary. Money was tight.
I went to several matches at one club. These were club matches, not registered matches.There was a guy there who won most of the time; later I found out he was a middle-of-the-pack shooter in the Southeastern Region registered matches.
Anyway, he had a rilfe built by a man named Charlie Joins, a very good gunsmith who lived the foothills of the North Carolina mountains. It was built on a Remington 40-X, with a Hart barrel, McMillan stock, Jewell trigger. All good, nothing special. Of course, Mr. Joins had been through the action. The owner allowed the barrel had close to 1,000 rounds though it, and explained that was on the high side, it wouldn't last as a winning rifle too much longer with that barrel.
Bobby (the man's name) wanted a rifle built by James Messer, at that time, a smith with a long waiting list. He needed to sell his current rifle in order to get the Messer-built rifle. I think he felt that this new rifle would help him move up at the sanctioned matches (it didn't).
Since he was getting a new rifle, he was also willing to sell me his dies. These weren't a bargain, but did save me having to figure out how to get dies -- in those days, a mystery to me. We also negotiated for an older Pat McMillan barrel fitted to the action. That barrel had about 800 rounds on it, but was too heavy on this rifle to make the 10.5 pound weight limit.
So, the price for the rifle, dies, extra barrel, about 4 pounds of Australian 322 powder, a mixed lot of cases, and a few other bits & pieces, was $1,200. To put things in perspective, a new Panda action was around $900 at the time, and the then very popular Hall action was around $1,200.
He also showed me a little about shooting benchrest, and wasn't a bad teacher.
OK, here's the point(s).
1. Charlie Joins wasn't as popular as James Messer at that time, but was a very good smith. I'd say as good. Charlie built Dave Tooley's rifles before Dave became a gunsmith.
2. A trued Remington 40-X single shot wasn't as popular as a Hall, but the accuracy potential was as good (I know there will be howls on this one). It usually does take a good 'smith to realized it's full potential, and no, the resale value isn't as high. But that's a plus if you're buying used.
Right bolt-left port was just coming into fancy; it was believed to be faster to shoot. At one time long after the right bolt-left port craze began, & maybe still today, Mr. Tony Boyer shot the old fashioned right-right, noting that it took as long to acquire the target as to reload, and a right-right meant you didn't have to let go of the bag (or joystick). In short, there are ways to shoot that can compensate for a particular mechanical setup. The last two actions I ordered -- new -- were right-right, because I'm comfortable with that.
You don't have to have a high-dollar front rest or even a windage top. The old Hart pedestal is still just fine. I have two joystick front rests, and find myself going back to the old Hart.
3. You do need a good scope, and *good* here means one that doesn't change it's point of impact. It has nothing to do with how bright it is. I don't know of any way to guarantee that, with a scope budget from $300 to $3,000. I would get a new scope, they all go bad over time, and while a new scope is no guarantee, is is a plus.
So that's the story, with some notes.
Recently, there was a long thread on why aggs are coming down. Most replies had to do with equipment. For the fun of it, I went and looked at the Southeaster Region Hall of fame, because I know these guys -- some new, some deceased. The older ones, by in large, didn't have a range at home. The newer ones do. Firing enough rounds to know were the bullet is going in the changing wind conditions is a lot more important than brand X Y Z equipment. All the equipment has to be is reliable, giving repeatable results.
Since you live in Chicago a home range is not an option, but the moral is the same. For short range success, don't chase equipment, chase shooting skills. And the hardest skill to acquire is, eye to spine (not brain) to finger, what's the wind, here on the ground, going to do to the bullet?
Good luck to you, and don't forget to enjoy the shooting.