Yah, having lived on a 105 acre ranch with 85 acres in trees, I would get a 60cc saw at least. There was really nothing that I could not cut down with the 361 on the ranch in OryGun, including 4 ft DBH trees. Hardwood and softwood mix. Lots of thinning and firewood cutting, and storm cleanup. If I had stayed there, I would have gotten a 372 or a 441 for the bigger trees. The 290 was a good starter saw, but the Olympyk was also running better then with a 24 inch bar on it. With the two of them I could cut anything. After I got the 361 to replace the Oly, the 290 became the backup saw. However, in hind sight a 5100s or a 260 would have been better to run with a 361. A light 50cc and a heavier 60cc combo is a good option. I ran the 250/210 saws for limbing, but they are just really not up to the task of larger acreage and timber management. Good homeowner saws though. If you have larger diameter stuff I would cosider a 372 or a 440/441. Otherwise a 361 will do fine. A 290 will do the job, but they are heavier and more tiring to run with the vibration. Also the longest bar that they will run well with is a 20 inch. A 361 will go to 25 inch, or even 28 inch with an oiler modification and skip chain. You can grow into it.
Ah, were that I had known about this site before I bought my first saw. But then I got the 361 pretty fast after that, so all was not lost, and a lot of better times felling trees was gained. I have to thank my ArboristSite brothers and sisters for that. The guy that owns the 80 acres that I am staying on here this week got a 260 Pro after using my 361 this summer. He loves it to death. The 361 was a tad heavy for him to deal with. He has a light frame. Most of the trees here are redwood, doug firs, tanbark oaks, madrone and bishop pines. Mixed hard and softwood, but leaning toward soft. A Stihl 260 with an 18 inch bar does all he needs.