Exterior paint color help

[Matt T.]

I'm under contract to buy a fixer-upper in a historic neighborhood, and can't figure out what would be best for exterior paint colors and general curb appeal. I'll be ripping out the overgrown shrub, replacing the upper windows and installing a new door. I'll also be scrapping and repainting all of the exterior trim, and at least the lower level brick. The lower level is painted brick, while the upper is vinyl siding. I don't really want to replace the siding since it's in decent shape, but could I paint it to help the house stand out? Any ideas on different paint colors between the upper and lower floors? Below are a couple of pictures showing the front in low/high light situations. Thanks!

[Matt T.]

Thanks for all of the advice. Since this is an older thread, we actually started painting the exterior last week and are finishing touch-up today and tomorrow. In the end we decided to go with a dark grey for the wood and brick to try and contrast the white and try and hide as many imperfections as possible (as there were many). I'll post some pictures here in a few days once the exterior is done. I'm not thrilled with how the choice turned out, but it does look much better than it did before.

A little more background, we'r rehabbing this as a rental property in what I would describe as a "C" neighborhood. There are no historic preservation regulations, but most of the houses were built in the 20's and 30's. It is in an inner city neighborhood in Oklahoma City within a mile of some nice, up-and-coming districts where houses are selling for $250-350k, but houses in this neighborhood are still pretty distressed and usually sell for $60-120k. We're doing a complete interior and exterior renovation to get the house in good shape, but the idea we went with on this one is "simple and clean" (and cheap!) so that we could get a good renter in place and hope the neighborhood continues to improve. If it does, we will probably do nicer renovations to the house in the future as rents (hopefully) improve.