I think you'll fail on both counts; securing a double entry Iranian visa (I have tried and failed), and getting a Turkmenistani transit visa when you're not transiting the country.
The Turkmenistan problem is simple to solve by booking a tour, the double entry Iranian visa problem may be much harder. I would be very interested to hear if you manage to get one as I've long wished to nip into the SW of Afghanistan and back into Iran.
And of course, you cannot re-enter Iran with a used, single entry visa.
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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.
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