what do you recommend?

The oregon sharpening set?

Electric models?

Also do you recomend sharpening on the saw or off?

I have a 16 and 14 inch saw with 2 extra chains for each

Now will i ever pay for it in sharpenings? No. Will I pay for it in convenevence and longer lasting chains - Yes. You see some shops keep me waiting for days or worse still some take off a WHOLE LOT of steel when they sharpen. A nice way to sell more chain, I'd say.

I have hand files, and a manual filing rig that clamps on the bar. I find the filing rig to be a PITA, so I sharpen them freehand on the saw. After several freehand sharpenings, the angle starts to wander, and the rakers need to be touched up. When this happens, I take it to the Agway and have them touch it up on their bench rig for $4 or $5. With two chains, and the frequency with which I use my saw, I find that I pay for a professional sharpening roughly twice a year.

I've thought about one of those nifty powered Oregon deals, but I doubt I'd live long enough to pay for a $200 machine at the rate I'd use it.

I've seen the rigs that let you use your Dremel tool, haven't ever talked to anyone that uses one, but that might be a good compromise.

I do about what you do regarding getting it done right. After two Dremel sharpens, I replace the chain with a new one and toss the old one (sharpened) into a drawer for emergencies.