This has properly been asked before, but i couldn't find any answers, so here goes.

When offering coaches contracts, if i offer two coaches the same position, and the both agree, who is signed? The first one offered, the highest ranked? Something else?

It's more or less random, if both coaches sign then the first coach that signs will immediately be fired. (There's no consequence to this but there is not a way to control which coach has priority)

Thanks! :)

Sure would be great if there were.

When did this change? I thought you could only offer a coaching job per position one sim at a time ..

same

You're right, I misspoke, my brain was thinking it acted the same as the FA contract form. When you make an offer to a second coach it replaces the offer you had for the previous coach.

I'm really struggling with coach contracts to the point where I just can't be bothered with the whole unnecessary headache of it all, so far I've given up 3 teams because of this and maybe about to lose another one, is there any way to simply this?

If you are unable to get a coach signed by a game, the AI will select the best coach for you - the only one that you really want to make sure you get is the head coach, the others are useful in terms of what attributes they improve the players on your team, so the AI will always get the best coach it can based on those attributes.

I'm open to suggestions on how to make it better, I know folks have mentioned queuing up coach contracts (so you can offer more than one and prioritize it) which may help solve it.

The easiest way I find to do it is to overspend for your Head Coach / OC / DC and then sign dirt cheap and young developmental position coaches.