It's probably possible, but in terms of the amount of time required in relation to the payoff, most of us are better off just running scratchbox in an old distro on a VM. E.g.
Silvio's vagrant setup worked for me last time I dabbled with N900 development.

I have tried a few times to come up with a new development environment which doesn't require scratchbox. Typically using a chroot with the N800/N900 rootstrap, using qemu, and patching in native amd64 binaries for things where extra performance is needed (e.g. compiler, gzip, etc). Following similar principles as described at https://mariusv.wordpress.com/2008/1...a-pot-of-gold/ , but without scratchbox at all. I never managed to get as far as bringing up X in such an environment. The scripts which start the GUI on maemo have special code which causes it to behave differently under scratchbox which lets this work. IIRC, they do something different not just with X, but also with dbus, which I never unraveled. Additionally, on modern Debian, the Xephyr display server isn't compatible with maemo's X libraries.

If I were to start building a development environment for maemo today, I'd forget about emulation, and just focus on cross-compiling. Obviously I have already taken a step in that direction. The trouble is, once you go down this road, it becomes impossible to take advantage of existing (unchanged) development packages from the maemo repositories, because many of them were built with scratchbox in mind. IIRC, the Qt moc is one example of this.

Continuing on this thought, suppose we had a cross compiler, and corresponding library development packages for a GUI toolkit (I like gtkmm on Diablo, qt on Fremantle). Using the same versions and build flags as used by the real maemo libs, so anything built with this toolchain could be installed on maemo with no additional dependencies.

Hmm, I reckon you'd also want a way to create Diablo/Fremantle compatible debs, which would be another challenge.

Would that make life easier for anyone here? Or just add another confusing development option?