I have a box of chains that look just like this or worse at the house .I got a 7/32 file in that guide and went around and touched up all the cutters with a few pulls , I can get more gullet on it later , but there was a noticeable difference pulling the 7/32 through after having sharpened with the 13/64 the last few times . it was a little dark for this picture but it is a little more open. but this chain was still cutting well
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If you say it cuts well like that, I think you would really enjoy a chain that had the gullet cleaned out and some hook on it.
It also looks to be very dull to me as the cutter is rounded at the one of the most crucial "points". It should be taken back until there is no damage left.
That chain looks to be a full chisel chain, but the corner is very rounded off. I would also agree that the rakers look as though they have been taken down to far, which would help compensate for the condition of the tooth, but is unnecessary if the tooth is sharpened properly.
For the length of a bar there are a lot of factors that matter to me, but your formula is about right.
On a 50cc pro saw I an 18 is where I like to be cutting max size of 10-12 on a normal basis, but I will burry it is it's less time than running to the truck to grab a 70 with a 20-24. I don't run the 60cc saws very often but I like a 20 on a 60cc pro saw but will sometimes run a 24 in softwood or if the saw is ported.
Is the chain on your 2255 and 18 and 20x325 or 3/8(picture looks like 3/8).