Maybe it is inappropriate to ask but does anyone have an opinion on Song Show vs Pro Presenter? 

I looked at switching over a couple years ago, only because of the popularity and community size of Pre Presenter. When we started with SSP 20+ years ago, it was the best decision, but in the past few years it has become unstable and the community seems to be shrinking. We have been fighting crashes with video backgrounds for over a year. Lately we need the NRSVue bible, which I started requesting 2.5 years ago, and still nothing real. I even offered to help fund development to speed things up :(

If you are starting from scratch, you can install both and compare yourself. If you are converting from SSP to PP, it's another story.  We are willing to endure the re-training required for a different system, but we have stayed with SSP because of the investment we have in our libraries - mainly 370 songs from the ELW hymnal, and dozens of psalms formatted for responsive singing. We tired a shareware program that used xml to transfer songs from SSP to PP, but the results were not good enough for us. We are very particular about how songs are displayed. 

So we will stay with SSP for now, with the hope that they can deliver a new bible, and stabilize their graphics.

After spending way too much time for a volunteer I think moving to ProPresenter is a sideways move.

SSP is a fantastic program, but with dwindling support and progressively unstable. When GoFish Media was available for support, most support problems could be solved quickly.

I'm afraid "the writing is on the wall!"

When I looked at it, a few years ago, I found the ProPresenter licensing model much more expensive. It seems like anything you wanted to add, as an add on. Also, their site license is a literal site. You're only supposed to use it at one physical location.