Hello Ben, I hope you're doing well today. First, my theory on the errors you were seeing are that your migrated SmarterTrack install may still be configured to connect to the old server. Can you try shutting down the IIS site and application pool for your SmarterTrack side, then rename the SystemSettings.xml file to SystemSettings.xml.old within:

C:\Program Files (x86)\SmarterTools\SmarterTrack\MRS\App_Data\Config

Once you've done that go ahead and start your site/application pool back up and use the setup wizard to connect to your new install of SQL Server. If that doesn't do the trick we may need to take a closer look at this here in support. As to upgrading to the latest release, this should theoretically work well! With that being said, if you'd like some assistance in evaluating your environment against our upgrade process please don't hesitate to submit a ticket and we'll confirm all of that for you. Let me know how it goes when you get a moment to test further. Have a good one!

Kyle,

Thank you for your response. I would have answered sooner, but Hurricane Isaias knocked our power out for nearly a week. Just got restored yesterday.

So, initially what I did was as you suggested (w/ v9.5). I removed the config file in order to trigger the Wizard, and the Wizard is the one complaining that the server could not be reached. This prompted me to think that maybe it just didn't work with SQL higher than 2008. So I attempted to apply the installation of the latest version to upgrade the system, and I get the following error when attempting to load the website:

Configuration Error

Description: An error occurred during the processing of a configuration file required to service this request. Please review the specific error details below and modify your configuration file appropriately.

Parser Error Message: Could not load type 'SmarterTrack.HelperClasses.HTTPHandlers.EditorFileHandler'.

Line 113:      <add verb="*" path="HttpHandlers/EditorFiles/*" type="SmarterTrack.HelperClasses.HTTPHandlers.EditorFileHandler" />

Ben, thanks for your follow up on this, and apologies for my own delay! Glad to hear you got power set up and are back up and running! Glad you found the issue, that would definitely do it! If you ever see that error on a fresh upgrade in the future be sure to try browsing from a guest session as well as this error might appear if your browser has the web components cached. For optimal results I've included some screenshots of how we set up our application pools as well below. The Specific Times configuration (for recycling) can be set to 3AM or another time where usage is minimal.

You'll see the Identity = NetworkService and the Managed Pipeline settings are configured for Integrated. Next, we make some adjustments to idle timeouts, recycling settings, and the start mode: 

Hope that helps! Have a good one!