Rewrite VS Redirect

I have 2 websites which use different ports but the same IP. One site uses port 80 and 443. The second uses port 8080. I would like to create a rewrite rule that will take URLs with {HOST_NAME}/<SecondPath> on port 80/443 for the second website and rewrite them to use 127.0.0.1:8080/<SecondPath>. This is failing for me as a rewrite but works as a redirect. The sites are completely independent. I am trying this without the ARR module installed. I did try this with the ARR module installed previously and it didn't seem to make any difference.

I have the following questions:

1. Is this something that won't be possible?
2. If a user does come in with an SSL request on port 443 will this cause a content mismatch error on the client?
3. Can I use redirect with 127.0.0.1 with external requests?

Thanks in advance