Hello Mattbibby!
I have not done this route, but I plan to do it starting from the UK in August 2016 so I have done some research. Please, if anyone reading this sees that my information is incorrect, I more than anyone would like to see it corrected!!
My main concerns about Iran were that as Brits we are required to organize a guide which is expensive, the visa is very tricky to obtain in the first place, also Iran commands by far the most expensive securities when applying for your Carnet de Passage. Tied in with the fact that the route to India from Iran requires navigating Balochistan, a region in Pakistan which is currently considered to be unstable, I found myself looking for alternatives.
Now, going north of the Caspian Sea doesn't look too difficult.
No visa required until the Russian border, which is about £100 for a 30 day single entry, need to apply before hand.
Kazakhstan - No visa required, 15 days from entry.
Kyrgyzstan - No visa required, 60 day from entry.
China - a tour company can sort out the myriad of things like a guide, temporary Chinese license, Chinese plates etc etc for you. The visa itself is £30, but I've had a few quotes and the cheapest it gets is roughly £900 per bike for the relatively short ride to the Pakistan border in a 5-6 bike group, plus daily living costs.
Pakistan visa looks difficult-ish to get but I haven't looked into that in much detail yet. Security issues - the route you would be taking is the Karakoram Highway, referred to here a lot as KKH, there's lots of information on this site about it and the general feeling I get is that although there probably are safer things to do in the world than ride this route, it's reportedly one of the most wonderful travel experiences going and not half as bad as the media will have you believe so I'm more than tempted. Cross into India then near Lahore.
You can usually avoid Pakistan via Tibet and exit into Nepal, but due to the earthquake there's no way to do that at the moment. There is a good chance that a secondary route will open to overlanders into Nepal in 2016.
I also got a quote for 24 days going through China into Laos with a guide, but the question is; do I want to be following a 4x4 for such a length of time on a strict itinerary at great financial expense, all the while missing Pakistan, India, Nepal and Myanmar? Yeah the guide through Myanmar is expensive as well but speaking for myself I'd rather limit the guide time, see more different countries/cultures, do more solo riding or non-guided group riding (whatever opportunities come up) and the more I look into the KKH the more I want to do it.