Originally Posted by
salvadors
But does backtracking even mean anything if you're just buying a series of singles? As long as it's an offered route, you're just stopping in the middle. It doesn't matter what your combined route might end up like, or how long you stop in any place, etc., right?
Backtracking only applies on each ticket, so it doesn't matter if you book 5 single tickets that backtrack all over the place, as long as there isn't any backtrack in the middle of each individual ticket!
I'm not best placed to advise on what routings will be 'allowed' you can always try and see since sounds like you are flexible. Sometimes it can depend on the call centre agent - but in general a reasonability test is applied and none of your options sounds too out of this world. If you check the miles on this website
http://www.webflyer.com/travel/milemarker/ then you can apply your own reasonablness test. If you have flights that are more than double the mileage directly between two cities then it might be getting to the dubious stage (though this is only a rule of thumb and may still be valid anyway)
To work out if star alliance flies somewhere you can use the *A website;
http://www.staralliance.com/en/travellers/index.html
You will find that Star Alliance (Turkish Airlines/Lufthansa only) flies to Ashgabat, so if you have a routing via IST or GYD (Azerbaijan) then it will work. If going somewhere exotic like this as your final destination you will find the routing becomes more generous as its difficult to get there, and you may be able to, for example, have a day in IST, as any stop in a city that is less than 24 hours doesn't count as a stopover.
I think you are best now having a look at the sticky in this forum on how to use the ANA tool and work out routings/airlines that work for your dates with business class availability. As you're doing a lot of routes, and sounds like you're pretty flexible I'd probably say book each route when you find the availability. Also have a read of the general forum sticky for tips on dealing with the call centre. I use ANA along with the Star Alliance website for bookings. If the Star Alliance website shows a routing then its 99% sure that it will be a valid one for bookings, though it doesn't show stopovers too well.
When booking something like this, is it better to do it all in one go (albeit step by step) or actually book each single separately? I've never done a redemption before (which is one of the reasons I have 140k miles in the first place!)
You have to book each ticket individually, however, you can book 5 tickets on the same phone call if you wish. The main FAQ has more details and tips on the whole booking process
As a PS... if flying a lot like you are then you can, if you wish, try out lots of different business products by varying your airlines during the trip if you like that kind of thing - it doesn't have to be all with the same airline!