It's definitely doable.

A few years ago I stopped relying on the community repos and just started building stuff from source.

I went for the LibreSSL fork of OpenSSL, and I have it installed side-by-side with the old OpenSSL version Maemp has installed, since their .so names don't conflict (0.9.8 is installed at .so.0, while the more recent libressl or openssl with version 1.x.y installs at .so.1).

Building LibreSSL from source was great because it basically has no dependencies. Self-contained, very easy-for-a-newb-like-me build. I imagine OpenSSL is just as nice.

Note that this won't just help upgrade all the other components "for free" - since they are different major version numbers with separate .so names things have to be recompiled against the new ones. (So for example I have latest `ssh` and `curl` and Python that I built using the latest libressl, but for example the old 2.5 and 2.7 Pythons from the repo still use the old 0.9.8 OpenSSL.)

Python 3.6 (latest at the time I last built Python from source) had a lot of dependencies. Since by then I was ignoring the repos for anything I built myself, I didn't bother checking how many I could already get for free, and just built everything that was needed to make it compile (or wasn't needed but seemed quick and easy, like latest `zlib`).

I built everything directly on my N900 at the time, so my experience is probably not very helpful for trying to build it in scratchbox or whatever.

I really ought to get a cross-compiling arrangement going, but that's just enough of a pain and investment that I haven't mustered up the drive to do it. Looking around here I see people have made strides to make the Scratchbox environment more conveniently accessible so maybe I'll use that. (But honestly I like building things on my N900, though the multi-hour compiles for things like nodejs aren't fun, and I never did get to gcc 5.0.0 because the compile would crash the N900 after a solid day of compiling even with tricks like a massive SD card for pure swap space and ionice+nice and disabling the watchdogs to get it from choking itself, hence me finally accepting that I need to embrace cross-compiling, if only to get the latest compilers on the N900 to keep the perversion going.)

Anywau in the meantime I have tarballs of everything I built, and if someone suggests a way to share them that feels low-effort enough to me I'm happy to dump them somewhere.

I can also share the `./configure` arguments I used just because those are always a good tedious 15 minutes to read through and decide.

And if you want I can check for any other steps outside the usual

1. unpack source
2. ./configure
3. make
4. sudo make install

workflow that I used if anyone wants, but for the most part it was that very regular workflow without weirdness, besides the standard Maemo 5 weirdness like prefixing half the install paths with `/opt/maemo`.