The Yak is the youngest DCS module and still in early access, so it is very much lacking in content at the moment.
There are 3 basic training missions available now:
1) Cold start
2) Taxi and takeoff
3) Landing
These are well made and will get you in the air together with the manual or Chuck's guide, but don't expect anything more in depth at this time.
IMO your approach makes very much sense in theory and if you really want to start with a prop plane then by all means go for the Yak. It is by far the most managable of the props in DCS.
If you are looking for a more complete and in depth training experience you might want to consider the L-39. It is very easy to handle, flies great and there is more content available, inclunding a very detailed DLC training campaign (Kursant).
Also both mentioned planes have dual cockpit multiplayer funtionality and it's really fun and effective to learn new stuff together with other people. So if you know someone that flies DCS, go for it. And if you don't, there are plenty of guys in the community willing to help. Just ask.
Have fun and see you in the skies!