I replaced my brickmolding with PVC. It will never rot and painted looks identical to the previous trim. Still, I need to touch up and inspect around the brick molding every year or two since mine gets the full force of the weather. If I could, I would use the modern J-trim around my windows. This is weather-proof and maintenance free. But my old lap siding is too thick for this product.

Fiberglass doesn't really bring anything to the table that cannot be had with the "Big 2", vinyl and wood. There are some excellent performing fiberglass products coming out of Canada, but most of the stuff state-side doesn't present anything compelling, again, unless it fits a narrow set of circumstances. The long and short of it is this: Wood is better at being pretty, and vinyl is better at being energy efficient, cost effective, and low maintenance.... These comments refer primarily to a full fiberglass product. If you are looking at fiberglass construction with a wood interior, something like a wood/ultrex Integrity, wood/fg Pella Impervia, and the like, I'd lump them in with wood clad products personally. Still have interior maintenance (primary risk is condensation), and you are choosing form over function. A full fiberglass unit is kind of the worst of both worlds (not as pretty as wood or as efficient as vinyl but still has the high price and generally lesser warranty), but let's say you want a painted interior other than white. If I was shopping for a window or sliding door that could be painted gray, I'd definitely lean toward fiberglass over wood. You lose the beauty of wood when its painted, and fiberglass won't ever rot.

Untreated wood shouldn't be in contact with masonry. Remove the wood and replace it with composite material or wood which is intended for the exterior use. This is a common problem in situations like yours or when regular and painted wood was originally used in bay windows etc. Here is an example just to give you an idea in a similar situation with a bay window where the wood was deteriorating an beyond including sheeting and its replaced using composite material.

Thanks everyone I really appreciate your help. I don't think I can get past keeping the brown brick as is. Again, I'm not an architect, so you have to use your imagination with my sketch. I'm thinking a light German smear on the brick with white board and batten. Still adding the cedar accents (pediment and brackets), adding a cedar pergola around the front door, and adding modern farmhouse awnings over the two windows on the front and the two windows on the lower left to give the house a little more dimension. Any thoughts or suggestions are welcome!