Evaluation should be performed from the perspective of the node invoking it. This is your first case, and it is the only one that really makes sense.
If you're testing your very basic engine against other complete engines then yes you can expect to lose every match. You are missing lots of techniques so playing against other engines is not a good method of testing right now. Once your engine is stronger then yes you can use this method to improve strength or perform regression testing.
I'd recommend setting up simple positions and playing with it manually to look at whether it can see basic captures, checks, checkmates, etc. Be warned that even with a perfect implementation of alpha-beta and simple evaluation that your engine will still blunder at times. This is because of the fixed search horizon so next you may want to look into quiescence search.