Hey- we are riding UK to Thailand via India leaving September (see Sep 17 UK to Bangkok on hubb). Brits have the same restrictions in Iran as you but if you travel as a group the costs are greatly reduced ($850 for visa letters, guide and ten nights accommodation). As for weather- staying south will be fine but it'll get a lot colder as you head north to the Stans (by the time you get there) and there are some high passes to cross back down to India. Note there are no ferries across the Caspian, only cargo ships which do not run to a schedule.
Have fun,
Chris
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