Clown&^%- I got the Dremel saw sharpening attachment. It works great. At Northerntool you can get an electric sharpener for like $35- I can’t vouch for the quality, but they have a variety of prices too (as much as you wanna spend).
I fully sharpen with the Dremel after 3 tanks of gas (my tank is a bit smaller than yours). I never remember to flip the bah. I put the stock safety chain through maybe 10 cord of oak before I got a reasonable chain.
With a 290 and a 16” bar, each tooth sees the wood a bit more often than my saw with an 18” bar- probably not enough to make a difference.
Remember- if it’s throwing “dust” rather than little chips or curls, then you need to take the depth down a bit on the chain. If it cuts at an angle all the time- that could also be the depth- at least that fixed that problem for me years ago.