What bothers me most is that the walls are three kinds of siding and the proportions of each are almost equal, making for a very awkward facade. To really improve this house, I'd recommend new siding to unify the walls or changing the finish to stucco which would allow you to frame out the windows and give them more importance. A light clean colour would show up well in this shady spot. White would work. Then the next priority in my opinion would be adding landscaping to take away the stark look of the frontage.

There's a larger remodel in the works in the next 5 years, so I'm going to hold off on redoing all of the siding. The front of the house is the only place with the 3 different sidings.

OK, glad you have a plan Ben! Best of luck with it :)

I think the siding mix will actually present as extra cottagey - look fresh and the gable vents are sort of charming - if you were spending that kind of money I would suggest new windows with the right muntins and better profiles for a little bungalow. (an evenly spaced mulled trio of single hung windows with muntins up top in the big opening would be more period appropriate and add a lot of charm)

I would try paint first. Contrasting trim paint on the gable would bring out some of the cottage charm potential you have here .. so would the right shade with some crisp trim. You can't go contemporary here, so dark is likely not the best. Why not play with classic cottage color and use an accent bright on the front door for personality? All white is classic and isn't too "sweet" for a guy. You could do a navy door that would read sort of traditional but also be fresh. If you do use white, realize that outdoors all colors get about one shade lighter in the full sun, and the ceiling whites and bright whites are wrong on a sort of historic house, since bright whites come from titanium / which wasn't around until the 1950's. You want an off white that is warm (not yellow, but sort of woody undertone) - it will read as a white but have depth and richness to it. I like Ben Moore Maritime white, you might want to test White Heron or swiss coffee as well. You'll want white trim with your white vinyl windows anyway, so test for that reason too.

If you want to test a gray for the body, realize that grays reflect the sky and read blue so you can get a very blue house without trying. Maybe test nimbus gray from ben moore or the next shade down smokestack gray. Nimbus has a faded blue jean / coastal blue gray quality that is particularly appealing as a light shade just to give contrast back to the white trim. Then you will want to keep all white even on the front door so it is classic.

If want to play with more of a Mod Cottage, you would use white trim, but go to a deep navy shade on the siding - something like van deusen blue or newburyport blue. Then a lime green door would be sort of fun.

I'm not thinking you are a little pink, yellow or pale green cottage kind of guy. Here are some photos .. .all white - albeit with mod windows and roof

Palma Plaza · More Info

Here's nimbus gray on a ceiling -

Beach Cottage in Oceanside · More Info

When you do remodel, building code and budget permitting, seriously consider wrapping the porch on the left side around and across the front of the extended left side of the house (with wider 3-part window) with a hip roof on the corner and a concrete floor -- at least as far as the right edge of that window. You seem to have enough under floor vents to be able to sacrifice a couple if need be -- or just leave the vents above the porch floor.

For now, you might consider a couple pair of shutters for the front windows that you could reuse when you get to your larger redo project.

Before you paint anything now, decide what siding and color for your siding and trim you want for later because you could then use that trim color now -- especially if you're going to go ahead and add the trim boards to the ends of the rafters that have none -- and then you may not need to repaint the trim again right away even when you change the siding.

You likely need to add a vent in that front gable.

https://www.google.com/search?q=gable+vents+images&biw=1366&bih=673&tbm=isch&tbo=u&source=univ&sa=X&ved=0ahUKEwj8rbWLtuTJAhXEXRoKHSbRBZwQsAQIGw

If your remodel includes any part of a new roof, consider a second, higher gable on the right instead of the hip corner on the right front corner. A gable enables you to add a vent for air circulation to help prevent moisture problems in the home.

http://bilinterior.com/wp-content/uploads/2012/10/gable-roof-provided-by-wilmington-deck-and-screen-porch-gable-roof.jpeg

I can think of several colors that would look wonderful on your house, light pink, mauve, light green. But if you are planning a siding change in the near future I would just live with it until you can afford to tackle the whole project. That way you will not be redoing your paint job in the future.

I would keep the current color and just paint the trim a few shades darker. Landscaping will have a far greater influence on your curb appeal. Then be sure to use window treatments that look good on the outside as well as the inside.