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As for Tech Wrecker, again, focus on trapping choke points. Maps like Mannworks, where you have baddies spawn on both sides then all move to a single side are good. Another technique is to have a spy sap a group (or scout milk a group) and wait for the group behind them to catch up to the milked/sapped group. Also, I would recommend using stock with crits and not scottish. That way there's no doubt that the damage was done in one detonation.
As for Sly Voltage: I don't play MvM Spy much, so I can't really speak for it.
As Sleepy Panda recommended, try wave 6/8 on Bone Shaker in Mecha Engie. Make sure the team holds the cave the entire time. At the very end, 11 pyros each with a medic come out all at once. Disperse your stickies, have full damage upgraded on them (crits is you wanna be extra-sure), and you should easily get the achievement. You could also try to reduce the variables that might be causing the bug - use stock instead of Scottish Resistance, try with and without crits, etc. I do think that there are some requirements that aren't stated in the achievement descriptions and that they can be bugged sometimes. The problem is that if they're bugged just for you, it is unlikely a widespread issue Valve will do anything about.
I have heard of people getting bugged achievement tracking due to some local Steam file that totally eludes me at the moment (just google "steam achievement bug reset delete file" or soemthing like that). I forget the name, but essentially deleting it will sometimes fix the problem. The only problem is that this file also tracks your progress on other achievements, like the 100,000 bots you killed toward the 1 million bots killed achievement will revert to 0. You won't lose achievements you completed, just progress on ones you haven't.
Good luck sorting it out.
^ This is long time buggged. I got the rest ok with no issues.
I only got Tech Wrecker after getting exactly 20 kills. I had done 10-14 kills multiple times and it finally triggered on 20. The achievement description was wrong for me and might be for others as well.
Just keep it to yourself.