Finally got the guts to do this.
When possible, start with a beard pic.

Then follow with one where you just look funny.

Then, start HRT.

Play with makeup.

Go shopping.

Play with hair.

Go casual.

Play dress up.

Have fun.

Wait for what's next.

4 1/2 months. Finally, the time, hormones and effort are starting to yield results for this 38 year old. Now, for the eyebrows and beard... still a long way to go.