A number of things about OpenShift make it more complicated:
1) I guess my biggest complaint is that it's entirely dependent on git. Probably that's fine, and even good, if you're a professional, but for the hobbiest it's another learning curve. I got it working well enough to install my software and make updates now and then, but I never mastered it (what's my "github-id", what's my "repository name" -- these were things I needed to know to migrate to their new version; probably trivial but not to me!). The ability to upload a zip file, open a CLI running bash, and unzip is really beautiful, as is the ability to just upload a new version of a file through a simple web interface when I want to change something.
2) And the more I think about this the more it annoys me: What kind of service is that, to tell your customers that you're changing your architecture and so they have to do a bunch of work or you'll stop supporting them? Crazy! Improve your architecture if you want, but keep supporting your existing customers.
3) Can't say that I understand what it is, but OpenShift has a "model" that you have to fit yourself into, which ends up meaning a handful of config files you have to set up. It's not just "name your program flask_app.py and you're good to go" like it is on PythonAnywhere. They're not necessarily especially hard, but the less I have to know about how the hosting platform works, the better. An example: my site uses a SQLite database. On PythonAnywhere I just put it in a directory under /home/xtiles, and I can hardcode the path to that in my program. On OpenShift I have to use a system environmental variable to figure out where it is -- not rocket science, of course, but also not as simple as '/home/xtiles/data/game.db' or some such.
And finally, I'll just add that I can't imagine this kind of support from RedHat, I really appreciate your concern both with my little problem and with making your platform all it can be.
(And thanks for the encouragement on the game -- I'm hoping to make it my retirement plan, so I love getting positive feedback!)