I think there's a reason why openssl keeps updating their old branches at the same time why new and there might be some binary incompatibilities and api breaking changes. In my oppinion we should rather update to 0.9.8y instead of 1.0.1e (they were published the same week, and each contains newest bugfixes, just in different branches). And, if you need 1.0.1e, you could package it e.g. as "openssl1" (i think in MeeGo Harmattan the "libssl.so.0.9.8" was replaced with "libssl1.so.1.0.0", so if we follow the scheme, we could have both openssls installed and the newer one could be distributed via extras).

If you're paranoid, you can never be sure And, Debian and/or Maemo usually add platform-specific patches for the sources, so it might be good idea to append those while packaging, too.