Hello Dani, I hear you and if I haven't written so, I feel your pain as I had to many years ago decide what to do with my share of a PC sales+repair shop. I was working 18+ hour days and while it made money I couldn't find techs that had the right skills. That's off topic so back to your burdens.
The infrastructure stuff is rarely what users see. It may be what you see but you are asking for feedback which is great to see. I'm not saying this is some twelve step program.
One of my life lessons about sales, and getting the contract is summed up in one line:
The above PAIN POINTS are all great so if the landing page was changed to not feel like you landed on a random page and the login was redone so it wasn't running off to another domain (hint: Powered by Dazah to maintain your investment there) then you may have moved enough for new members to not feel as lost when they first get here.
Hopefully you can put the pain points on cards then assign a cost and benefit value to each one. When I was on larger development teams we did to assess which features we would implement first or another term we used was risk management. While some ideas were great the cost was too high and thus the risk would be higher. If the cost was low and the payback was possible it's risk/reward value made it more likely we'd do that earlier.
When things are borked you know about it soon enough. You have Dazah but for DaniWeb, maybe it's DaniWeb, Powered by Dazah to reach your other goals?