It's doable
I don't use a vise or clamp or anything like that, just the saw. sit the saw down flat. I use my generic bubba tailgate work bench and a stump to sit on when not in the field. Now, notice distance between bottom of bar out at the tip and the flat surface. Find you a chunk of wood from your wood pile a little larger than that distance, say an inch or two or whatever works for you.. Now when you sit the chain down rest it out at the end on the block of wood, that will prevent the chain spinning on the bar.
Now look straight down on top of the cutter, you'll see a little line that follows the cutter angle. That is the witness mark. Follow that angle that way, plus your round file slopes uphill just a smidgen. If you pick the correct chunk of wood, you can get the saw to tip sideways a little and cover that angle as well. Only file one way-in. Keep the file straight, don't flinch and round it off at the end of the stroke. You can get several cutters now without moving the chain. Once you run out of your comfort zone, just reach over and pick up the end of the bar, then with your other hand slide the chain forward another section of cutters. Do that until you are done. I haven't marked my chains, I can see and feel when I get to the original cutter I started with, or you can just count, whatever. I mean, a sharp cutter is different from the dull ones, duh. When done, flip it around, do the other side. One side will be clunkier to you than the other, depending on if you are left or right handed, just be careful and get both sides the same, as much as possible. I have no set rule on number of strokes, just what it takes, 1 to freeking 8, usually two or three for me. Depends, too many variables on what you just cut.
The depth gauge/raker I file with a flat file first about every other or every three times I file and always before I do the cutters. No need to go nuts with it, it has to be around 20-25 thousandths lower then the cutter, that works fine, try to get them all even with each other down the loop. Follow that little angle there so you don't get binding.
That's it. No real voodoo to it, just tedious. Once you have enough muscle memory from doing it, you can just about do it with your eyes closed.
$5 will get you started in two brand new files, a round and a flat from the saw shop. Get the right size for your chain. Don't know what size chain you need sharpened, so that's a variable.
If you have a hard time seeing the cutters, you can always get one of those hobby magnifying glass things that are mounted on an adjustable bar. I think they are like ten bucks from any of the cheap import tool joints.
The other option if ya want is just switch to the new oregon powersharp system, I will attest it works as advertised. Cost more than a regular chain of course, and you have to get a new bar to start with it,(you need the whole kit to start, bar, chain, sharpening stone and holder system, then after that a new chain comes with a new sharpening stone) but in five seconds you go from wicked dull to near brand new sharp. They show a video where the cut a cement block with it, I mean dull the snot out of it, "rock the chain" is the common term used, happens to everyone eventually, a few seconds later it is back to sharp. I ain't kidding, it is that fast. It's different from regular chain as it sharpens from the top instead of the inside, but it *does* work and it does cut wood just fine.
I think they only go up to a 16 inch bar and chain system now, but I know they are working on a 20 for larger saws. No idea when that will be released though.
For small time joe homeowner just a few cords a year, either way, two files or pop for the self sharpening system once and be done with it. No need for a multi hundred dollar grinder just for a dozen sharpenings a year or something.