Thats not real Iran - there is no point just going to Kish, unless you really are just collecting countries or stamps. Its an amazing country and going to just Kish would be just wrong.

Turkmenistan - you do NOT need to be on a guided tour for a tourist (non-transit visa) on arrival. You just need an invite letter and someone needs to pick you up. You can then kick around Ashgabad on your own. I used a local agency, booked the letter, got the visa on arrival with that, they booked me 3 nights in the hotel Altyn Asyr, and then dropped me off at the Iranian border, I think all in, that cost about $350. About half of what StanTours wanted.

Lots of people I met in Mashaad, Iran were getting their transit visas for TKM there too, it was very easy. There is a wonderful guesthouse there with the owner being a wonderful source of information, and who organizes trips into the countryside. In Shiraz, one of the things not to be missed, is a night out with the nomads in the hills - these are not tourist nomads - these are the real deal, when we arrived, we were the first visitors to their "house" in 3 months.