Choice of non-standard ephemeral ports

This is somewhat related to - but different from - Recommendation for a non-standard SSL port .

One answer there suggests that binding to 8443 is a valid example of an alternate HTTPS socket configuration. However, under some Windows systems, 8443 falls within the ephemeral port range.

My questions are:

• Are there any risks associated with binding a service - such as sshd or httpd - to listen to a port in the ephemeral range?
• Could it interfere with the creation of outgoing sockets? In particular, will a listening socket and a connecting socket on the same address with the same port interfere, collide, or otherwise fail?
• Is it expected in such a case that a client request a new ephemeral port until it finds one that is available?