Great question, actually- and the answer is: whatever makes you happy. I'm the who tends to compartmentalize as well. I'd never put eggs on my plate with pancakes and then pour syrup, for example- hate it. I also prefer my cheese to usually "not have stuff in it" so I don't often slather it with other things.
If I am making a cheese board purely for tasting cheese, I pair very little else with it. Usually just a small something with some acidity to help separate the flavors and to scrub the fat off my palate. I then tend to eat one cheese, then something non-cheese, the another cheese etc... and often the bread plain.
For example- cheeses plus a little bread, acidic pickle like cornichons and maybe a tiny bit of dried or fresh fruit ala this plate served at Mission Cheese:
That's 3 cheeses, about a light ounce each. On the small board to the right is bread, dried fig, some dried apricot (maybe one whole) and a few corinchons.
If I put together a big board for an evening dinner in a social setting I find most will take a little of everything and smash it all together. I try to assure that everything on the board works OK combined with anything else to avoid train wrecks. Like cooking, how to combine cheese and other flavors is a learned process - by now I have a decent sense of what goes with what so if friends are over I tend to make the board pretty goof-proof: you can combine almost anything and the result is at least good... while some pairings will be really good and I might suggest somebody try it that way. It's a good way for people to try cheeses that they think or know they do not like plain.
But don't over think it. Basic pairings that work with most foods work with cheese too: sweet with salty, savory and sweet, for example. Jams and spreads are always sweet... so they almost always pair well with just about any cheese as cheese tends towards salty and savory. Using a jam that is savory, like walnut butter, fig, dried date... are nice compliments with any cheese but really can help to tone down strong cheeses like Valdeon,,. that pic I posted a few days ago of aged Gouda, whipped honey and butterscotch toffee... great trio... but I'd not have put that together if I had a really strong blue on the plate. but drop the candy and add some dates and it all would work.
The harder ones are the stinky cheeses some are so strong that any strong jam etc may just get to be too much... so I always try a little first.
Does that help?