I have toured the campaign many times in order to complete absolutely everything there is. Every map, every contract, every objective. It was no-doubt a hassle, but I still think it's worth it even if I didn't need to do all of it.

That being said, I've been around the map rotation long enough to know which waves of which missions have enough Uber Medics to fulfill the "5 Drops at Once" criteria for the Expert Sniper, Expert Demo, and +2 Contracts. My biggest complaint was that there were never enough at once and I didn't know where. Luckliy this should help people out if they know what to do, but don't know where to look.

BE WARNED: You usually only get one shot for these instances, so make it count and PRAY your team doesn't interfere. Also, it's only UBERCHARGE Medics. While drops of Shield Medics, Kritzkriegs, and Vaccinator buffs may count (the latter two only if you're VERY fast) and will help you in cumulative Uber drops like in Expert Soldier or Advanced Demo, only the stock Uber Medics are plentiful enough in one spot at some point to fit this criteria.

Anyways, here are the instances. If I left out something, let me know, but also give me a screenshot for proof. I wanna believe your claims, but I won't unless I see a screenshot. The first person to do so gets a free robo-cosmetic. Nothing major, but it's still a free cosmetic.

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1) Ice Breaker, Wave 2 (Shiverpeak): There are 3 Giant Demomen that spawn in at around the midpoint of the wave, and they have 5 Uber Meds each. The remaining 8 are from the Giant Buff Banner Soldiers that drop in. You'll be able to get all of them in one go if you wait until they both drop, but only attempt that with Demo, and if you have a Scottish Resistance (for more stickybomb placement), preferably crit-boosted. This way, you'll have a larger Margin of Error in case they space out, but you still need to pay attention and act on it. It's hard, but possible. This is also the ABSOLUTE BEST spot to grind for it due to there being 3-4 chances (class-dependant) and the fact that it's still early in the mission and wave, so no need to plow through any other waves besides the first or a butt-ton of robots just to even try.

2) Mannstorm, Wave 5 (Maelstrom): The 4 Giant Heavies spawn in with 5 Uber Meds each, and this all happens relatively early. The first a little after a Giant Buff Banner Soldier (who has 3 Ubers of its own) and the remaining 3 after a bunch of Super Scouts. They come in succession one after the other, and that starts after the last Giant Bonk Scout dies. This is the second-best spot due to high concentration, but it's on the second-to-last wave in the mission on one of the more-challenging maps.

3) Fiber-Ops, Wave 3 (Sequoia): 2 Giant Shotgun Heavies (or "Obese Scouts" as I call them) spawn in with 6 Ubers each. This is the third-best as it offers some leeway in case you miss one, but it's at the very end of the map, after many Crit-a-Cola Scouts, Crit Pyros, TONS of Banner Soldiers both normal and giant, and the fact that the Obese Scouts spawn in shortly after a Tank, so make sure your team has either a plan, or REALLY good DPS.

4) Coldfront Coalition, Wave 4 (Shiverpeak again): 5 Ubers on a Big Heavy. Nothing much else to it.

5) Scabby Subordination, Wave 6 (Calico): 5 Uber Medics each on 3 Giant Backup Soldiers. Unfortunately, this is only possible with Demoman: the Explosive Headshot upgrade, as good as it is, is still affected by the Backups' damage blocking. Uber Medics each have 150HP, and a maxed-out EH deals the best range and 190DMG per target, instantly killing Uber Meds. But the Backup blocks some of the damage even if it isn't critical, only dealing 123 damage per target, leaving them with 27HP and subsequently popping Uber, since they always do so if their heal target is at 60% max health, or if they're at 54HP and below (look it up if you dont believe me). So the Scot's Res for Demo will only work there, and even then you'll want maxed out damage upgrades and as many stickies as possible.

6) Driving Training, Wave 5 (Trainyard): 5 Ubers on a Big Demo. Pretty straightforward.

7) Ultra Uplink, Wave 3 (Underground): 5 Ubers on a Big Heavy. However, there's also a Backup Soldier and a Gas Passer Pyro with the Explosive Gas Passer upgrade accompanying it without them being displayed on the HUD. Same rules apply as in the Calico section, but now you also have to either be super careful, super preemptive, or super fast after using an Uber Canteen.

Well that's it for now. Hope it helps people. Again; let me know about any I may have missed, keep it to Uber Medics only (the rest either don't Uber, or there aren't enough at once), and the first person who sends me a truthful note that I missed WITH SCREENSHOT PROOF gets that free robo-cosmetic.