good guy, they make a filling guide, that's simply a U shaped peice of steel, about 6-8" long. it sits over the chain and shows you the angle to file at, and it also has relifs that show you how much your rakers are worn.( the little bump infront of the tooth)
you don't want to file the rakers too much, or the saw will tend to grab things on you, and kick. i think the gage shows 0.035" below the tooth hight. other then that, your chain looks good. the very tip of the tooth is what gets dull, and you can usually see it.
it is better to file a saw evey couple hours, with 1 or 2 rubs, then wait 8-10 hours and have to file it alot to get it sharp.
those dremel sharpeners are nice, but i find it only takes 4-5 min's to file and service a saw anyway, course i used to work in the woods at one time.
that old 5000 is a great saw, we've got 2 of them, and they have been the toughest saws we've ever had. thier comfortable to operate too. mind ya, i like my 257 huskey a little better, but if i hadn't cut wood for a living, i wouldn't have bought it.