Do you have more photos of the house?

Your house has lines and detailing appropriate to what is is. Other than the replacement siding, it seems fairly original. It's quite possible that it had some timber details (knee brackets) on the roof overhangs at the eaves and gable. But even without them, it's textbook bungalow.
My suggestion would be to learn what color schemes were originally popular for bungalows, and select within that palette. Warm, earthy colors were favored; blues, grays, whites much less.
Casey

I agree with Casey. Paint would help a lot. Something rich and earthy. Google bungalows and you will see some great examples. You house really is nice looking!
Diane

Hello everybody! I did not expect this good response!

Macv, here are a couple of pictures if you have any additional input. The back of the house faces another yard, and is only distinguished by a solar electric array (and there is no backyard at all).

The color I am thinking of painting the house is Compatible Cream (now, thanks to macv, probably on top of shingles rather than lap boards). It is a Sherwin Williams color that is kind of mustardy-yellow. Thinking trim portions would be white, porch blue or gray, to be determined, not sure. While I do love those cool colors, as you can see the weather takes care of all the cool one might need. Also, I don't want too many colors--this house doesn't have anything like those lovely Victorian details that I'd need to highlight.

Thank you powermuffin, it's nice to hear my house looks reasonable, I've been throwing money at it lately so that helps.

Casey, I'm pretty sure the siding is original and probably was never much fancier. The rest of this old neighborhood is pretty much in keeping with what I have. There are two reasons I want to replace the original siding--one, it is deteriorating and at least one painter has declined to paint it, and two, I would dearly love to insulate. So I respect its oldness and love that about it and do not want to eliminate its character in any way.

Thanks so much everyone!

This is the belt line I referred to earlier with the siding above it flared out over it. It is very important to keep this detail.

I've never know a two story house to be called a bungalow or for that style to have a belt line not that it matters.

Thank you macv! I will think about this and how best to work with the detailing I have.

Ooh la la! Great shingle example, macv.

Pamela, how are your boards deteriorated? It may be that there are too many thick layers of paint, and painters are worried about getting one more coat to adhere well? There is a house in my neighborhood owned by a pro painter. It's over 100 years old. The last time he painted it, he had his crew scraping and sanding like crazy, often to bare wood. Some boards were replaced. I have never seen such a thorough prep-job, but, then again, the owner was a pro, and probably keeping his crew busy between other jobs. I'm not sure anyone else would have been willing to pay going rates for that much prep work. It was probably triple the cost of a standard paint job when all was said and done.

I wonder if painters are turning down your job because it would similarly require intensive prep to be done right. Maybe they just want to spray and go to the next job. But if you could get someone to bid on it, sanding, scraping, board replacement, the whole nine yards, it might be cheaper than new siding, and future repainting would not be so expensive, unless you let it go too long between paint jobs. I'm not saying this is what you should do, but you might want to consider it.

Also I don't see how keeping existing siding precludes insulation. My house had insulation blown in from the inside when we were repainting rooms anyway. From the outside, they only have to remove two clapboards; one high, and one low, to blow in.

You have solar panels to save energy. There is an energy cost to produce new siding, and to dispose of your existing. Considering this might be one more piece of your analysis.

I think you have a beautiful house and great taste. It's nice to see another old house owner who takes the time to research before starting a major project. I'm sure the results will be beautiful no matter what you decide.

Slateberry, thank you for the nice comments!

It is true I only talked to one painter. What put him off (and thus me) was lead abatement requirements in legal terms as well as regarding safety and expense. I don't really know what it would cost but he made it sound stratospheric.

I am waiting for a bid now for fiber cement shingles which I'd paint, and I will continue to explore other options. Right now, thanks to help from gardenwebbers, I am obsessing about historic colors (thank you old_house_j_i_m) and details (thank you macv). I haven't looked into real cedar, but I might. I'd like to see how appropriate the fiber cement looks first. It certainly sounds easy in terms of maintenance.

Also, thanks for the insulation tip. My neighbors just removed their siding (replaced stucco with vinyl) and insulated--they said their heat bill was $100 less last month. I like the way that sounds!

Lead abatement? Interesting. I live in the greater Boston area, and I don't think there's a single house in my neighborhood that doesn't have lead paint on it, yet they all get painted and maintained. Pro painters deal with it every day; any one, at least in this area, that is intimidated about dealing with lead paint properly when working on a house wouldn't last long. Maybe you just need to talk to another painter.

When another one of my neighbors diy'd his house, he had tarps everywhere while he scraped/prepped, wore a mask, and eventually discarded the clothes he wore for the work. All the tarps that caught the chips were rolled up, bagged, and taken to a facility. But that was ten years ago; maybe the rules are more stringent now. I'm sure the web will tell you.

More and more, I find pros want you to do the job their way, which may not be your way, and generally they don't want to reveal the real reason they don't want to do what you originally asked for. So I talk to more people before I have something done. The things I agreed to when I first bought my house---oof! Never again.

slateberry, apparently there are EPA rules going into effect in April. To tell you the truth, I am trying not to find out too much about this and just hope when the bid comes in for new siding I can go that route rather than having to think about paint guidelines. But we will see as it evolves. As you know, old houses always have something new to tell you.