> Kris,
I suspect that the design differences between the N85/1.4 and the N100/2.8 macro are so small in everyday photography as to be of no consequence in the end. Yes the macro lens may be both sharper and more contrasty but that doesn't really matter. If the image is too sharp, it can easily be made softer with any number of softening filters, not least of which are the Zeiss Softars in one of their varying strengths. By the by, I have tried several different types of softening filters and find the Zeiss Softars to be most to my liking. If I could afford more, in different sizes and strengths, I would buy more! Back to the lenses.
If I were in your position, I would be making my choice on the following basis. I tend to shoot portraits hand held with available light in low light connditions. With the 85/1.4 this means that I can get away with shooting at 1/90 sec, and sometimes with certain Contax bodies at 1/60 sec, and an aperture of 1.4 if I need to. Using the 100/2.8 I need either 1/125 or 1/90 sec and 2.8. The difference is a minimum of two stops and a maximim of three stops. This is the crux of your decision. If you can shoot on a tripod and your subjets aren't moving, all of this is irrelevant. In that case you may as well get the 100/2.8 and soften the image with a Softar. If available low light is your environment of choice, the 85/1.4 is irreplacable and the macro just won't do when 2 stops means the difference between getting the shot or not. What and how do shoot? There's your answer.
As to your second question regarding film, I regularly shoot with Fuji colour negative film and it is my film of choice. I use NPS, NPC, NPH and NHGII/NPZ. I do use Kodak Portra VC films but only in certain lighting conditions and only when I have to. Yes, the film makes a big difference, especially with portraiture, but so does the lighting. Try the NPS (low contrast film) in contrasty lighting. Use the NPC in overcast or flat lighting. NPH handles contasty days well but also works fine in flat lighting as long as you give it a bit more exposure, try 320 or even 250. NHGII/NPZ are good in low light and have good contrast and saturation of the light is flat but exposure comments for NPH also apply here. None of these films like much in the way of underexposure so be warned.
You simply have to try the films in the camera/lens outfit you end up buying and see how it performs. Do you like the results? If so, stick with the film/lens lighting combination that you know works the way you want. As a final comment, because of the variation brought about by the printing process, after all every print is a particular printer's interpretation of the image on the negative, you need to find a good pro lab and stick with them through this learning process. If you change labs, or even use a lab whose output varies from operator to operator, you'll get lost. Find a willing subject and shoot lots of film! Good luck,
Gary.