I basically just added "link=shared" to Boost and "shared" to the OpenSSL helper scripts in the appropriate section. This produced files about 2mb smaller (each), but still way bigger than Bitcubes (6mb vs 20'ish).
Ive made some tweaks to OpenSSL's and Boost build options and testing right now too. Looking at GMP now too, to see how possible it is!
RE: Compiling Steem for Windows (on Linux host)