Is the Bugaboo Donkey worth it?

Short Answer: If you can afford it, yes.

Longer Answer:
First, let us begin with a small video so you can see what the Bugaboo Donkey is all about...

When I was pregnant, all of my mom friends told me to invest in a good stroller.  Those who had bought a good stroller said they were glad they did, and those who hadn't told me they regretted not doing so.  The Bugaboo brand has been popular for quite some time in Europe, but it was propelled to international superstardom when the press reported that a Bugaboo Chameleon was purchased for Prince George (prior to his birth).  These strollers are not cheap.  The Bugaboo Donkey retails for about $1300.00.  (I'll just disclose here that my father bought ours as a gift for the baby - after telling me it cost more than his first car.)

Why did I decide on a Bugaboo Donkey?
The reason I chose this one over other strollers is because of the mono/duo combination.  You can have two babies in this side by side (instead of one in front of the other, or one underneath the other as with some strollers).  I really wanted this side by side option as opposed to the others.  Maybe because when we lived in London I watched so many babies looking like they were being bounced off the steps of the tube as their mother tried to carry the stroller up and down stairs.  The great thing about the Bugaboo Donkey is that you can have two children side by side - and they can both be front facing, or both rear facing, or one front and one rear.  I just love these options.
The Bugaboo Donkey also comes with a bassinet style seat for newborns, as well as the "regular" seat.  (Note - to make your Bugaboo Donkey a duo you have to purchase the extension pack as well as additional seats).
The other big factor in getting a Bugaboo Donkey was the resale value.  Because the Bugaboo Donkey comes at a hefty price tag, there is a big demand for used Donkeys.

PROS and CONS

Cons: I will start with the cons.  First, obviously, the price.  It is an investment.  With regards to the stroller itself, there are a few things that I would love to see improved.  The seat has two positions - one which is almost completely upright and the other reclined.  I would love to see one more position added somewhere between the two.  I would say the Donkey's biggest drawback (aside from price) is its size.  This is not a compact stroller.  If you drive an SUV of minivan you may be able to fold this up and easily fit it in the trunk, however in both of our vehicles (a four door car and a pick-up truck) we have to remove the seat and basket before folding the stroller and putting it in the trunk.  It is not difficult, just another step that takes a few seconds.

Pros:  This stroller has lots of storage space which I love.  You have the side basket as well as the basket underneath (which easily holds a full backpack as well as other items).  We can load it up and motor.  The adjustable handlebars are great for someone like myself who is quite tall.  They also allow for more compact storage when the stroller is assembled.  The sunshade provides excellent coverage for the baby.  The stroller moves well in all terrains and I have also found it easy to use in the winter.
At the end of the day, and going back to the main reason why I wanted this stroller, what sets the Bugaboo Donkey apart from other strollers in its class are the seating options (mono/duo/twin) which are well illustrated in the video above.

In a nutshell:  This stroller is quite large so make sure it can fit your vehicle for transport.  The seating options are what truly set it apart from other comparable strollers.  It is quite pricey but has a good resale value.