Thanks for the response folk...
I have gone through all above responses, your plan is very pragmatic and I pray for its success, a "Men's Cup" indeed. I wish I could join you 
I will reiterate that one of the bigger issues is arranging of a "Carnet", I am no expert on this subject but well understand that this would be the most critical part of the journey...
Now, coming back to Pak Iran border issue: Imo, entering from Tuftan is almot a NO-NO because of security situation. No one, either from military or from local tribes, can assure you a safe passage.
From past many months I was thinking into the possibility of crossing the border from Gwadar side, but apparently there were no formal border crossing other than Mund near Turbat but that was equally dangerous, if not more.
Last week, I travelled all the way to Gwadar and then to Pak Iran border and found the route much more feasible. As a surprise, I found out that a new road had been built from Gwadar to Pak Iran border, 77km, which is actually a good news. I could not make it all the way to the border customs area because of a bad patch which my humble Cuore did not look like to cross. And there was too much smugglers activity mainly smuggling fuels, imo with the connivance of authorities. However, smugglers look like harmless unless you disturb them. From Jiwani, I tried talking different people, one gentleman told me that there is proper customes on the border, but I could not ask for the timing. Local Balochs dont even require a visa and can travel through a Tahseeldar issued permit. Iran-plated vehicles are not a rare sight in Gwadar and Jiwani...
Hope the above helps
Take Care and have a great great trip :
