Okay, this is easy to understand.

So maybe the best is to handle the trips day by day through the hotels. But I'am a bit concerned about this chinese holiday thing in the first week of october. Maybe it is hard to get a driver last minute. Would prefer to make some appointments before we start our journey.

there are black cab companies where its a per head price but you need to keep luggage light. there is a company near the train station in the city center. renting a private driver would be extermely expensive...

What do you mean by "extremly"?

I would like to have several stops on the ways. To see some scenic landscape or tourist attractions or something. Do you thing i could this with a cab driver without haveing the same price as with a private driver @ the end?

black cabs dont stop. it will be 3 people in the back and the driver and another in the front. seats are firsr come first serve. private driver youll be paying for gas and time.

so i guess we are looking for a private driver.

Seems to be the best to have a different company for each leg.

03.10. Kunming -> something beautiful -> Dali

05.10. Dali -> something beautiful -> Lijiang

08.10. Lijiang -> something beautiful -> Shangri-la
+ 09.10. Daytrip Shangri-la area -> Airport DIG

So maybe three different operators would be good.

It seems that english speaking drivers are rare.

The cars are going to cost more then 400-500. Just the gas and road tolls from Kunming to Dali alone cost 400-500! You still need to pay the driver for his time. And he has to return to Kunming empty-handed. You're looking at more like 1000.
Just take the bus or train!
However, also keep in mind you're traveling right during the middle of China's annual Golden Week, the worst time of the year to travel. The roads will be packed, hard to get tickets, hotel prices skyrocket.

High speed rail train to Shangri-la will finally be completed and in operation this year. Five-hour trip from Kunming, passing through Dali and Lijiang train stations obviously.

It is now indeed! For more information on the new train connection, check out GoKunming's latest article:

www.gokunming.com/[...]