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So the last two times I have faced my friends imperial guard as orks I have been annihilated by turn 2 and turn 4. He will usually bring 3 chimera with 2-3 flames and a Meltaguns gun in them, a couple of vendetta with Meltagun Squads wyvern artillery, and some leman tanks. I usually field 3 20 man boy squads with Shootas and Rokkits and nobz, warboss, couple bike Squads, couple Battlewagons and maybe a Stormboyz squad with lootas. Is it even realistically possible to win against a guard list like this. I just feel like orks literally have none chance to 2-3 flamers per squad after they have had to bunch up to assault vehicles or after wiping a single unit, after half the squad is killed by overwatch.

Guard are hard to fight. My brother plays guard from time to time and orks are the only army I play.

What I try to always do is take a couple units of deffkoptas. Outflank them and use rokkits to strip hull points. I also try to take as many transports as possible. I also love the morkanaut even though he is over costed and never makes his points back. The kff bubble can help protect units. Taking da lucky stick can help against massed guard fire and non ap2 weaponry. Tankbustas also help out a lot. Two units of those with 3 bomb squigs each can do some damage.

Other than that against guard you get d3 out flanking units from mogruks boss boys formation. I haven't used them against guard bit out flanking deff dreads or nauts.

To be honest I have played against him plenty of times but I am still usually 1 for 3 against him. Sorry but we play orks the comic relief and punching bag of the grimdark.

I'll be honest with you, IG are actually in a worst spot as an army than Orks right now so while I'm not saying they're a cakewalk they can definitely be taken down reliably by a properly built Ork list.

First thing is that you have to keep in mind is that chimera only have a side armour of 10, that means they either have to bunch up together to hide their sides (which limits their mobility) or have it exposed. Lootas are definitely good in popping transports so you have to be smart in deploying them on a good vantage point. What kind of terrain (if any) are you using in most of your games? If there's any kind of elevation you want to keep them there so you can keep shooting without having to reposition. As mhalko1 said, a group of 8-10 tankbustas in trukks are another good way of popping transports and vehicles.

I would highly suggest putting a few painboyz in those boyz squads of yours as it gives you that crucial FNP against mass amounts of wounds that guard can put out. Also are you putting your boyz in the battlewagons? That can help mitigate the flamer hits so long as you keep your distance until the guardsmen in the chimera are forced out. I would send the battlewagons after his leman russes while the rest of your army takes care of his troops.

Make sure you upgrade your boy's squads nobz with power klaws as they are our anti-everything took and ensure that even when most of the boyz die that they're still a threat.

Deffkoptas are also great for zooming onto enemy backfield objectives and disrupting backfield units like the wyverns you mentioned. Either scout them behind terrain and move them to engage with the wyvern or outflank them. They're also great for maelstrom of war if you play that game mode.

The problem with me fielding Lootas is that they are always targeted first and usually either get 1 round or none shooting. The problem I've had with sending my Battlewagons is that while the Orks destroy something on the charge they are demolished on the next turn by the bunched up chimera, flamers, and artillery. Also if the Vendettas with the melta Squads come in before I can make it to their lines then it gets even worse for me, especially because they have AV 12 front and sides and the Lootas are always dead by that point.

I'll have to look into getting more Tankbustas and using them but again they're just Orks with Rokkits (always the problem with special orks). Should I just give up on assaulting, I'm coming from 5th edition and this random charging, Flamer overwatching, and challenges really seem to make the Orks awful especially with I2. Losing orks as I charge and then always getting more Orks taken off in the actual fought is just really discouraging.

Also how are guard in a bad place, I don't think orks are in a bad place but against this type of guard they stand very little chance of doing anything.

speed, numbers, and playing to objectives.. boyz in trukks, wash and repeat. stop trying to footslog your boyz and just ante up and get a few trukks. while awfully explodey, they are cheap. its easy to field a ton of trukks pilled in with boyz. whats great with the new codex is that most everyone got acces to the trukk as a dt. hosting all your tankbustas, meganobz, flashgitz and even lootas in trukks alongside the trukk of boyz is a great stealth tactic. try running bigmeks with bikes and kff to give those trukks invuls. if your willing to fork the cash or experiment with kitbashing then you can put your best units in fw warkoptas which are fast, have decent dakka and can jink.
when you get nobz for your squads try using the cheap big choppa instead of the expensive powerklaw. the nob goes at the same initiative as guardsmen and the ap5 will help slaughter. the bigchoppa is just as effective at popping chimeras as a powerklaw (better since their is no risk of exploding the chimera).

Tankbustas are more than just "orks with rokkits". For a start they have tank hunter, meaning any hit that didn't pen, can be re-rolled. Secondly, they have bomb squigs, upto 3 shots hitting on 2+ then re-rolling to pen. Thirdly they have tankbusta bombs, str8 ap1 armourbane, re-rolling to pen.
Basically, they are death on legs for tanks. Using 2 squads of 10 I tore through a squadron of leman russ' and a bane blade in a couple of turns.
Chuck them in gunwagons, rather than battlewagons and you are set to rip guard to tiny bits.
For added shenanigans, take a weirdboy. Most of his powers compliment busters really well, especially da jump and kill bolt.
At a recent tournament I murdered to opponents backfield armour with a unit of bustas with weirdboy, jumping into their deployment zone and wrecked face before jumping back out.

Also, don't worry about losing Boyz, they're 6 points each, its not a drama. The point is to absolutely drown your op in Boyz. Pain boys will help mitigate losses, and when you strike back you will destroy any guard unit, guaranteed. The whole mindset for orks is that losses will happen, it doesn't matter. Have lots of viable threats, rather than deathstars, and don't sweat the small losses.
There are lots of good synergies with orks, check out some batt reps, and read some tactica, especially on the waaagh forum, and you'll be busting guard heads in no time.

I agree with the overplayed useful Ness of lootas. When I'm not rolling a1 or 2 for their shots they get targeted first. Now against guard I don't take them. After a few games with them my brother now fields all tanks with 14 front armor. Now they are useless.

Also agree that tankbustas are not just rokkit boys. I wouldn't agree with talking 10 squads. Take 3 5 man squads to Spam bomb squigs. Then when you have left over points bump up the squads 1 man at a time. Many times those 3 squigs are enough to pop most tanks the first turn

So does anyone have tips on taking out Vendettas? AreDakkajets evenworth fielding against him or should I just field 3-5 Traktor/Smasha gunz.

Also I feel like running trucks with boys is asking to get 2-4 Flamer templates placed on top of it and a melta(which is in every squad mind you). Also I meant that whill they have sweet rules, they're still a base boy with a6+ save, however I'll definitely grab some more.

Dakajets with the extra supa shoot a and flyboss are extremely good. 9 twin linked shots, hitting everything on 4+ is refreshing for orks.
That said, a couple of traktor kannons are great for taking out flyers, hitting on 4+ with ammo runs and grounding with +2 to their check can be devastating. They are also very cheap compared to the dakkajet. The jet, however, can shoot at anything reliably.
Horses for courses, try them both if you can, see which you prefer.