In your conditions, no special regular expression characters are used,
if [[ $checkServer =~ "is running" ]]; then if [[ ! $checkUsers =~ "are 0 out" ]]; then
In addition, you need to use the !~ Operator for the second condition: you have too many arguments
So you can use glob templates.
if [[ $checkServer == *"is running"* ]]; then if [[ $checkUsers != *"are 0 out"* ]]; then
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