I heat with firewood and cut mostly Hickory with some occasional oak, locust, and white ash mixed in. I've found that I usually break a tooth off before I get down to the indicator marks on the top plates, but that really depends on the saw. 45-50cc saws not so much, but 60cc saws with .325 chain yes. Once I break a tooth, the chain goes in the trash. When it starts getting "close" I set it aside for stump'n.
I've used hand files, dremels, and carbide burs to sharpen my chains over the years. When I hand file, I use the guides like the OP has. If I don't I've found that I have a tendency to let the file go a little too deep. It produces a really sharp edge, but the edge dulls pretty quick. Those guides ride on the top plate and keep me from making that mistake.
For the past few years, I've been using a Timberline sharpener that uses a carbide cutter/bur. Several years ago, my dad had given me an old Arnold Precision sharpener that he got back in the 70s. It used the same carbide cutters as the Timberline, but his cutter was dull and he stopped using it because he couldn't find replacements. His 3/16 cutter still had some life in it so I used that on my .325 chains for a while. When he gave it to me, the Timberline wasn't out yet. I looked into having some custom carbide burs made, but it wasn't going to be cost effective for the small quantities that I would need. The Arnold Precision has a lot more adjustment to it, but the simpler design of the Timberline makes it a lot more cost effective to build. I can't imagine what the Arnold Precision would cost today. If it I didn't already have the Arnold, I wouldn't have spent the money for the Timberline, but I'm glad that I did. I think there are some Chinese knockoffs of the Timberline available for a lot less. Often times, the pictures of the clones have the Timberline name and log on them (ie some of the pics aren't even pictures of their own device). If you buy a clone, pay attention to ANY possible differences to the Timberline. You want to make absolutely certain that the guides will accept a carbide cutter with a 1/4" shank. I put the cutter/bur in my cordless drill and run it on low speed. It leaves an absolutely RAZOR sharp edge, its quick, there's NO heat build up, and it keeps the same angle and depth on all the teeth. The only thing I really needed to do to it was to drill the guides out and install a 1/4" hardened drill bushing. The (replaceable) guides on the Timberline are aluminum and it doesn't' take long for that round hole in the aluminum guide to become an oval. They offer them now with a bronze bushing installed, but the hardened drill bushings that I installed are MUCH better. The only warning I'll give is NEVER spin the carbide bur backwards. It will instantly chip the teeth on the burr. Also don't drop them. They are VERY brittle. You can get replacement carbide cutters on ebay from the same company that makes them for Timberline. I need to get 6-8 them (lifetime supply) in the sizes I use so I'll have them if they ever go out of business. I've gone through 4 chains with them and only worn out 1 cutter, and that was largely because I spun it backwards by hand shortly after I got it.