DISCLAIMER: I'm perhaps just above novice level. I'm 63 (only been cutting wood for the last 10 years- I can feel that it's more work now, but I still feel capable with what I do/have).
EVERYTHING is a compromise.
I won't try to assess what others do/have done, nor will I try to tell anyone on what they should get or what they should do*, but I WILL explain my perspective as a homeowner who faces a lot of varied wood-cutting situations (none, though pertaining to saw-mill type work).
* These should be, however, universal "shoulds":
1. Proper protective gear (ALWAYS, EVERY TIME when intending on firing up a saw!);
2. Bars and chains in sound condition (no hard kinks in chains, no bent bars [or bad nose gears], no mushroomed bar tracks [ought to be filing as necessary]);
3. A Sthil chain sharpener as has been mentioned several times in this thread;
4. Proper escape routes;
5. Wedges and hammer/sledge (essential for felling, and good to have when you get your bar stuck [I'm a LOT better and NOT doing this now]).
My chainsaw work is almost all about cutting for firewood (for personal use): currently averaging about 5 cords for a heating season- I need to cut, on average, 5 cords of firewood a year, but I don't get around to doing so every year in which case I might have to do about 10 cords. Felling is infrequent, though from time to time I have that need. Trees are primarily Big Leaf Maple and Alder: then Hemlock; have some Fir but I won't touch it. I tend to allow Mother Nature to do my felling: felling is a very dangerous operation- I've been up in clumps of Maple felling multiple trunks- it's got all the feel of driving a big fuel truck on a road with heavy traffic and a bunch of motorists tossing cigarette butts out their windows... I've read a bit and watched a bit.
My wood can be wet or dry. Those saying that one shouldn't require much use of dogs isn't cutting dried/hard Maple! But, yes, in general, a saw should pull itself into the wood (chain digging in and doing what it's supposed to do).
For me, wood can be standing or down. BOTH situations are likely in places in which there's a lot of brush and tree debris (you should see the mess of a huge, 5 1/2' dia, Cottonwood made that recently crashed down on my property!). This is where you ensure that you make your working environment safe by clearing around the area, concentrating on ensuring that you can move your feet around w/o getting tangled up. When a tree is down, and especially twisty ones with a lot of branches, such as my Maples, limbing work is really a LOT of work- big saws are not your friend here as you amble though such; but, too small a saw and you're going to be spending a lot more time- longer cutting times means more time for something to go wrong, not to mention flat out taking longer. There's a fine balance here. And the type/condition of the wood can dictate what saw is optimal: I like to use my Sthil 192 for limbing smaller and softer wood like Alder.
More equipment means more stuff to keep maintained, more parts to stock (or not- discovering that you're dead in the water because you thought you had THAT part for that saw, but you didn't). I have only TWO saws. I've already noted that I have a Sthil 192. And now on to my main, "compromise" saw...
Given my above notes on what I cut, the saw that I came up with is a Husky 562xp, woods ported. I run an 18" bar and chain: I'm not tall, so bending over is a bit less problematic- longer bars allow you to bend over less. I've got a 24" bar but that is only used in rare occasions (I know I'll have to use it on that huge Cottonwood that recently came down). I've read of folks running as big as a 34"/36" bar on one of these, but I dunno about that. 18" bar handles 90+% of everything I do. If I only had one saw this is the only one I'd need.
As to how to know if a chain is sharp or not... Look at the wood chips it's throwing, or not! If you ain't tossing chips then cutters are dull and or the rakers are too tall (keeping the cutters from getting into the wood and biting). And look at the cuts. Imbalanced side-to-side sharpening results in scalloped cuts, and scalloping will bind the bar and chain in wood, especially with larger diameter stuff. The Sthil sharpener does very well in sharpening cutters and managing the raker height, but it cannot do anything about keeping a person from over-sharping/under-sharpening one side of the chain. Rectify by sharpening up just one side of the chain.
A loose chain can bind on the bar if you get some "english" going on in your cut- perpendicular forces against the chain, which causes the bottoms of the links on one side of the chain to bear down harder on the bar (this will tend to also mushroom the bar track). Probably worth mentioning here that a properly operating chain oiler is very important (dry chains mean more heat and more binding).
I struggled with my Sthil MS192 (it was bought with the wife in mind). What I thought was bar and chain issues was operator errors. I found that smaller diameter stuff was easier to bind up by unknowingly twisting the saw (imbalanced sharpening as well), causing the bar to bind in the wood, and causing the chain to also stress against the bar track. IMO, smalller/less powerful saws are less tolerant of optimal operating conditions- chains really have to be sharpened right. You can't brute-force them: although not a good idea, sometimes with a bigger saw you get into situations in which you just have to brute-force it in order to finish [unsafe to stop]). In general, I found out that the MS192 isn't a felling saw- ha ha!
For a smaller saw I like what was suggested above: Echo CS-370. Looks like a nice saw. But OP is looking for a "larger" saw, so unsure that this would fit the bill.
Here's my 562xp being used by an actual pro (former logger- a friend who did this quick job for me- too close to the road and I wasn't comfortable getting up in trees [still ain't, but I now understand how to approach doing it and am able to]; RIP Ralph!)
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Here's my friend back in the day, being an actual logger (NOT firewood saws!):
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