Does it make sense to go the N900 route now? Anyone has any experience on this? Some worthy successors like Pyra and Neo900 are coming out, and N900 can be still found easily to use while waiting for these newcomers. How good is Maemo these days?
An obvious alternative is to get a Nexus and install CopperheadOS + FDroid. The ecosystem is very polished and lively, plus hardware is very good albeit with planned obsolescence due to the lack of long-term kernel updates.
Also; the Mer wiki mentions an Android compatibility layer and you manage an Android emulator; would either or both not solve the Whatsapp issue?
Pretty much yes. With developer mode on you gain access to a terminal with bash and other expected utils. There is a mobile terminal application with custom keyboard which is more or less usable, you can also ssh into the phone without any problem. As for the package manager there is pkcon (probably some alternatives are also available), you can install build utils without any problem.
I've been using Jolla for some time before moving to iOS. It was a very cool experience. I really liked having a phone that I could hack and mess around with. The gesture based UI was nice, it was amazingly comfortable after getting used to it. The main drawback was the lack of apps and the reliability of the phone. The Android apps work poorly, they are sluggish and plenty of apps are not going to work due to lack of Google Play Services. Also with Android apps you get the old flawed Android permission model. The phone crashes from time to time, sometimes in the least suitable moment (stability varies between updates).
I must say that, while still needs some polishing, Sailfish OS (which is not 100% free, but is quite there, and provides a complete Linux experience), does the job. My Pebble works, my BT car kit works, and I have all apps I need. In fact, my biggest complain is about the hardware, being underpowered and with an atrocious camera. An official port from Jolla to some mid level device would make me _very_ happy.
In some countries, like mine, the FOSS mobile OS killer has a name: WhatsApp. Without official support for FFOS or Ubuntu Touch, and being very aggressive against third party apps (banning their users), most people can't even think of them as an option for daily usage.
Jolla goes around this bundling a commercial Android Dalvik emulator. Not the best solution, but one quite pragmatic.