This is not the answer I was looking for but it shows
excellent judgment. 1 point to you.

In fact, this was my solution not long ago when I discovered
my new prop doesn't back well. I'm planning a installing a
new rudder next year to mitigate the problem somewhat.

Backing out is easy because you have the option of a spring
line to control the alignment of the boat. Backing in is much
harder with boats with less forgiving keel/rudder/prop configurations.

wrote:

Realize you don't always get what you want, at least not necessarily
when you want and so: go into the slip bow first;