Hi @justin-zollar_1098 ,
At first, it looks like debug-level logging is enabled, so I would definitely disable that under Admin > Advanced Settings > Diagnostics.MinimumLogLevel. It should be 20.
The most common reason for a SQL Timeout (i.e. if you google the problem) is a SQL query that is taking too long. That shouldn't happen in Otter, but it sometimes does, especially when there is a lot of data and some non-optimzed queries.
A SQL Timeout when starting the Otter Service is unusual, and it may not be related to SQL queries.
The first thing I would check... are these queries actually taking that long to run in the database? You can use a tool like SQL Server Profiler or resource monitor, which will show you what's going on. You can then try running those queries directly against the database, and see if they're also taking an eternity.
It's very possible that SQL Server isn't the issue at all. It could be network related - and we've even seen some bad Windows updates trigger some strange side-effects to the Windows wait handles.
Best,
Steve