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i have a husqvarna e440 with 18" bar. im cutting some down red oaks that fell couple years ago. they are like 16 to 20" around. theyre big and hard. ive sharpened my chain like 3 times and even file the rackers down but cant get a good chip and kind of burning through it. thinking i need a bigger toothed chain but can i do that? also looking at a used husqvarna 51 and a sthil ms270. bigger saw that has a 18 or 20" bar that is more for the big stuff. can i put a bigger cutter chain on my 440 saw?
As others have said, close detail photos of the cutters on your chain will help- but there is absolutely NO SHAME in not getting the perfect file until you learn the technique that suits you and the timber you are cutting- absolutely 100% none of us were experts in the beginning and if like me you cut a lot of softwoods- you can get away with murder damn near in the filing and still do okay, hardwoods are more demanding.
As for a bigger saw and bigger bar- I would drop any ideas of the MS270 like last months milk. The 51, maybe- but you could do a lot better.
I would be looking at 60cc saws or better. Something like a 262, 266 (365)Husqvarna- or 034, 036 (MS340-360) Stihl.