Profile of CartoonVillain

In fact he cut my resources! So going for Cutoffs instead of trying to hold ground?

I did relatively good in unit preservation but it didn't help me much. And due to the fact I constantly struggled to hold territory and control my fuel I had my Schwerer Panzer HQ up when his Pershing hit the field. So I guess I did something horribly wrong?

Any tips with build order or how to cut his resources? Harassing all over the place maybe?

I'm not a great player, so this may be totally off the mark, but it sounds like your Schewerer HQ was too late, possibly the Luchs too. Did you go straight for Mech HQ or Medical first? You need to fight tooth and nail for at least one of the fuel points, spam mines on it, MGs, do whatever to keep hold of it, otherwise you will have no late game with OKW.

The Luftwaffe doctrine is good, as others have pointed out. Try to spot his staging area (where he parks his ambulance), spawn a FJ squad next to it when he's not paying attention and destroy it if you can. That will hurt him a lot.

Also, never stop (de)capping if you can. Once you force a retreat, try to (de)cap as much as you can before he comes back. Have a kubel ready and harass any territory you can when his troops are elsewhere. This will tax both his resources and his micro.

Pardon my ignorance, I've not been playing the game for long, but why can't the T-34/76 be at tier 3 with an increased cost, such that it arrives at around the same time as Pz IV's?

Now are they easier to use, I'm not sure. Are they easier to take in hand, yes probably. but it wasn't the case a year ago and grinding up the ELO system your friend will discover that overcoming an artificial lack is sometime painful.

I doubt he will bother with 1v1 or anything, he's a casual comp-stomper.

And by 'obsolete' in mean in the 'enjoyment to play' sense. Let me explain.

A friend of mine started playing the game 1-2 weeks ago. So he started with Soviets since the campaign is about them, etc. We did some comp-stomping together, but yesterday he said he wanted to try something different. So I suggested USF. After a couple of matches with USF he said he finds them way easier to play than Soviets. Not easier in the sense of winning, but easier in the sense of comfortable to play. And that's exactly the feeling I got when I switched from Ostheer to OKW.

Everything in the WFA factions is so streamlined, the game just flows naturally:
1. No base construction, so your initial engineers are free to roam the map planting mines and causing trouble.
2. The OKW mech HQ can repair vehicles so you don't need extra engineers usually. USF tank crews can jump out and repair their own vehicle.
3. Kubels can cap and attack.
4. USF weapon racks allow you to customize your riflemen/rear echelons as you like.
5. Volks can get Schreks and riflemen can get zooks so they continue to be useful even when vehicles hit the field and even vet faster this way.
6. The OKW medical truck can reinforce and heal and be a forward retreat point. The USF ambulance can reinforce and heal and move around. No need to build a separate bunker and upgrade it just to get healing OR reinforcement like Ostheer need to do.
7. The resources spent teching are actually put to good use since you get the OKW trucks with awesome functionality or the USF officers. I think this is probably the most important point, because you make an investment and get something useful back. By contrast, the Ostheer is stuck in Age of Empires times with HQ upgrades that feel like artificial tech speed bumps - spend resources for the opportunity to spend resources.

In a way WFA kind of ruined immersion for COH2 since for me the vanilla factions seem to belong to a long forgotten RTS age, while the WFA ones have all the cool new toys.

Thoughts?

If you have to pay fuel for unlocking incendiary grenades or for shreks you either delay the Luchs or you run a high risk to loose the early game.

Yeah, I understood it better after your original post. Without these tech speed bumps OKW seem to be a bit too flexible atm, and I'm saying this as an OKW player.