if you want to see molecules localized to the plasmamembrane i would use any cell membran dye (cellmask, cell tracer .. etc... there are a lots of)
If you want to see colocalization of two molecules, you have to use other methods like FRED or something similar. Anyway, I'm no expert in colocalization though
You can use any of the anionic channels that are specifically present in the plasma membrane. I used to used TMEM. Distinguish using two color and image it using the confocal or epifluorescence
For live cells, CellMask Plasma Membrane stains are best. If you need to fix and permeabilize, then I recommend wheat germ agglutinin Alexa Fluor conjugates (label after formaldehyde fixation THEN permeabilize and follow up with any other labels).
The main problem is not related to the labelling of the molecules with different dyes and using different methods. It is due to the resolution of the detection method that you use.