You need to decide how much you're willing to spend and when you're willing to spend it. Be warned, a 2 saw plan often evolves into a 3 saw plan, and then a 4 and 5 saw plan. At that point, CAD has taken hold... Realistically, you need to consider how long you run a chainsaw when you're using them. You may not use them frequently, but if you tend to run the saw for 8 to 12 hrs at a time when you ARE using them, you really need to be willing to spend money on the pro models. If you're taking 15 min to make 4 cuts to clear a limb or trunk out of a laneway, and cutting for a few hours at a time to get a few loads of firewood, then you might want to trim back your budget and save some money. Personally, when I'm running a saw, its often an all day endeavor so my advice will reflect that.
I'm not familiar with your 201. My opinion is that powerheads that are lighter than 10 lbs are often so week on power that they aren't worth owning. For that reason, the 026/260 family of saws is as small as I'm normally willing to go unless you're talking about a top handle which can provide other benefits. Thus, I would start by looking for a used 261 in good condition for a reasonable price. I do not own a 261 (yet), but at 4 hp, I'd say that it is an absolutely excellent choice for your small saw. If you like using your 201, don't sell it until you have a saw that you like using more than the 201.
From there it becomes a question of how big do you really need to go. I also haven't run a 400, but it's looking really impressive on paper. It's a nice step up from a 261, and would make for a great choice for the bigger end of a 2 saw plan. I'm shocked that Stihl recommends a 20" guide bar for the 400. With a 20" bar, it would be an extremely fast saw for bucking firewood. I'm not sure how long of a bar the oiler will handle, but I suspect that it can handle at least 28". That's enough to handle a 4' log once in a while.
Sell the 291 as fast as you can. It weighs as much as a 362, almost as much as a 400, barely has more power than the old 026, and less power than the 261. I'd also avoid the MS360 family of saws. I have a pair of 036 saws and I love them. Multiple people have run the 036, MS360, and/or MS361 have been disappointed with the 362. Realistically, with the 261, and the 400, this line of saws is becoming obsolete as a professional model.
If you really need to run a guide bar that's 25" or more, but the need is infrequent enough that you can't justify buying a saw to do it, then I would consider a Chinese G660 (066 clone). It's a lot heavier, but at 92cc it will easily run a 36" bar. Mine normally wears a 28" bar with a full comp chain. It's heavy enough that I'd rather not run it, but if I'm going to do much cutting in wood that's over 20", it's worth dealing with the extra weight. I often use mine to noodle large rounds in halves or quarters so that I can lift them onto my splitter. Whether it's Stihl or a Chinese clone, you don't save much money going down from a 90cc saw to something in the high 70s. On the used market around here, a MS460 sells for just as much, and often more than an MS660 in the same condition and the MS660s are easier to find. On the clones, the G660 and G466 sell for the same price. For me, I'd rather have the bigger saw because on rare occasion I do need to run a bar that's 36" or more. For me It's worth dealing with the extra weight of the power head so that I have the extra HP when I need it. If I were constantly needing to run a 25" or 28" bar, I'd add a lighter 70cc saw to my collection.
On the clones, do your research before you buy one. They are great saws for the money, but their is a reason you can buy them new for $300 or less. There are a few parts that you should swap out for Stihl replacements right off the bat. The work is straight forward and easy, and the saws are developing a pretty good reputation from those who realize that you're not going to get something for nothing. Personally, if my 026 or my 036 died on me this weekend, I'd order a blue replacement immediately. Then again, I'm not afraid to wrench on my saws, and I have a few extra saws to use if one of them happens to be down. If I were not willing to wrench on a saw, and had absolutely no interest in ever owning more than 2 saws, I'd likely avoid the clones and be willing to spend 3x more money for a new OEM saw. FWIW, I've never bought a brand new chainsaw. For that matter, I've never bought a new car, tractor, lawn mower, or tiller either. The only new gas powered tools I've bought are string trimmers.
I could have gone either way on the 462 vs. 400, but the 462 wasn’t at my dealer’s the day that I went, and the 400 handled very nicely. I have a 20” bar on it right now and a 25” for the occasional larger tree. Between that and the 201, I think I am set.
