Any advice on a job search?

I drive for Quicksilver (the courier company.) It's a small company, and the people are great. As of now, I think we have (VERY ROUGH ESTIMATE) maybe 20 or 30 class b drivers, and 4-6 class a drivers. (AGAIN, THIS IS A VERY ROUGH ESTIMATE. I AM LAZY AT KEEPING UP WITH OUR NEW DRIVERS). Nothing if not willing to help in any circumstance They have been generally honest with me (outside of the initial pay potential, which was VERY optimistic, but not totally unrealistic, like some carriers. That was 4 and a half years ago, though). I started in a class b truck (a bit of a heap, freightliner curtainside) but eventually found myself (after a few years) in a semi. Early, I drove mostly an International day cab (which was just ok...reliable). Eventually, I ended up in a Kenworth T680. (Don't tell my company this, but this is WAYYY more truck than they need for the occasional night out of town. I cannot stress how much I love driving this thing. SOOO comfortable, ergonomic, easy to shift. GREAT visibility (awesome mirrors that don't block traffic on perpendicular roads you're trying to turn onto. GOOD GOD I LOVE THIS TRUCK. GIVEN AN APU AND A FRIDGE, I WOULD LIVE IN A T680 AND BE HAPPY). I can't stress how much I love this truck. If it weren't for this truck, I may have quit much earlier (P.S. I haven't quit yet).As of today (10/8) we have two sleepers, my beloved T680 and an International (Prostar, I think. It's ok, drives nice enough. Not as comfortable as my GODSEND Kenworth, but really totally fine). They have VERY recently (within the past week) shuffled the office a bit to allow our awesome truck dispatcher (JJ) to take over some more duties related to trucks. They have a new guy(Tim, not new to the company) take over the day to day dispatch of trucks (all of them, class a and b). I'm sure this will will be fine, after the kinks are worked out. The new guy is definitely friendly, helpful, and totally willing to listen, just not sure how long it will take to dispatch local runs in ways that make sense. I'm sure he will get it running well quite soon (it's only been a week or so) seeing has how he has JJ as a good backup.
Here's the basics: people so far, including management (so far, 4 years and 7ish months in) are generally awesome. Haven't had a problem at all with anyone. Benefits suck ###. NO insurance whatsoever. I'm sure that they have the basic workmans comp, but nothing else. Also, vacation pay is terrible. I get one week a year (5 days) paid at $75-$80 (I can"t remember it exactly) a day. So basically (if you drive a class a mostly) maybe 2/3 of your pay for a week. Any time I've requested off has been given to me, no questions asked. (The latest I've given them is 3-5 weeks notice for vacation time, I think. The last time wasn't a whole lot of notice.)
So here's the crutch. Last year, driving mostly my BELOVED T680 (lots of lumber to SW Colorado, 2-3 day trips in the summer) I made about 49,000 pre tax. I wonder if (without any proof) that was almost a fluke. I did run quite a few insulation runs to nearly all parts of Wyoming (the company moved their HQ to SD, so those runs have unfortunately ended.) (I think, but am far from sure, I was the highest, or close to highest, paid driver at the company (this is purely subjective, but I think an educated guess.)) As of October 1st, If my previouse pay averages out, I'm on pace to make between 40,000 to 45,000 this year. My numbers aren't great, don't have a pay stub in front of me, but last time I figured it, that seems about right.
Bottom line: I get the impression that they have hired a few new class a drivers. So they must be hoping for more class A work in the near future (been pretty slow on that front so far this year). I'm not really sure what kind of income you could expect from this company with a class A. (The last year I had on solely class B (straight truck work), I thnk I finished with roughly 36,000 ish pre tax (don't quote me on that, I'd have to go check my w-2s). That's with anywhere between 8-12 hour a day,M-F (depending on how busy they are). I've spent a fair amount of time hopping in whatever class b (26,000 lbs straight truck) was available to do local stops a few pallets at a time (which is the bread and butter of the business). Most of our customers (Hydrofarm, esp.) are awesome, some others (unnamed) are ####.
You'll be treated well. The people are generally great (even if they don't know ####, they'll transfer you to the few poeple who do.) The pay is pretty mediocre unless you catch some good Class A work. The benefits are nonexistent (outside of very mediocre vacation pay). If you have actual trucking questions, you may find a driver or two to help, but this is primarily a courier outfit who happens to run trucks. You're kinda on your own for specific questions (although the office will be happy to help find the answers if they can, although basically no one there has trucking experience.)