Hi, on point 1 you are correct. We have overlooked this and we feel stupid because of this. However, the good news is that this is already fixed. We are awaiting for Apple's approval.
On point two - unfortunately this is how Chrome works. However, you can control HSTS via chrome://net-internals/#hsts. Unfortunately, this will not work for preloaded entries.
We will be issuing guides soon.
1) the certificate generated by Proxy is 512 bits which OS X doesn't support; and
2) i'm not sure that Proxy will work with sites that use HSTS -- you might be able to clear the HSTS database in Chrome, but still for sites like Google, I think the certificate information is hard-coded.