Basically, it seems you're trying to decide whether you want to implement the compression as full inline compression (2) or parallel compression (1). Many plug-in compressors nowadays include a Mix control that can let you set it for regular inline compression (100% wet) or dial up parallel compression by mixing between the pre- and post-compression signals. If you use a compressor with that feature you could set it up as in (2), and then experiment with the parallel compression you describe in (1) by simply adjusting the Mix control.

I know I sound like a broken record but thanks again. I am going to simplify my approach and do as you suggest - using it inline. Appreciated.