The problem with binaries from apache.org is they are built on Visual C++ 6.0 (VC6), we build our binaries with Visual C++ 2008 (VC9), they are not compatible. So our OpenSSL upgrade is not compatible with the Apache.org server. Your options are therefore use our 2.2.22 which is compatible, or try and find a VC6 build of OpenSSL 1.0.1 and as VC6 is from 1998, the chances are slim.
The config file error is because openssl.cnf file is not in c:\apache22\conf folder. This is where the Apache build process puts it, so that is where we set it to be. This can be overridden by setting an environment variable;
set OPENSSL_CONF=C:\path\to\openssl.cnf
Some day in the near future hopefully for those that prefer binaries from apache.org, they will start having 2.4.x binaries for Windows that will have OpenSSL 1.0.1. They will also be built with the current version of Visual C++. The person that supplies the binaries has spoken out on the subject and was waiting for OSSL 1.0.1 to come out. However, as with all binaries on apache.org, there is no rule internal to the project that states they must supply binaries, those are done on a per volunteer basis, if someone wishes to.