If you plan to keep it long term, I'd start by putting it on a concrete slab foundation. What it's currently sitting on doesn't look very solid. A pile foundation has to be below the frost line or you'll get frost heaves.

Hard to advice on windows, because it depends on the interior. If it's sited with a great view, you only need windows on one side and the ends. You can use shrubbery to hide any unsightly side.

I'd paint it to coordinate with your house.

Yes it will be renovated after it is moved onto a permanent base which will be in another yard. Not where our home is

What a wonderful find. I don't think you can determine where to place windows until you know where it will sit, what the views from different walls will be and how you will have the interior designed.

(I lived in a bungalow that was smaller than this - 3 people, 3 dogs, 2 cats).

You will also want to check out building codes. You usually need two exit doors.

I love small homes that are painted fun colors, but the neighbors may not like it as much as me.

Give us some idea as to where it will be placed, what the neighborhood is like and what your preferences are.

Fortunately we will have lots of options.

It is on a well treed rural acreage.

We thought to maybe do a "mountain" type cabin . Spray paint the siding black? Maybe with wood trim?

The current size is 24 x 32. Thought to maybe expand it to 24'x40'. We have no set floor plan. The interior will be stripped of the blackboards & bulletin boards of yesteryear :)

black is hard to maintain and may get awfully warm (absorbs heat).

What is the material of the siding?

Vinyl can warp if it is painted a dark color.

Yes that's a good point about black however we are in Canada and we do not get the extreme heat of the southern US.

And yes the siding is vinyl .

While it's a completely different type of house, I like the paint combination in this Behr inspiration picture. I wouldn't install a black roof. I wouldn't paint anything black.

Cool Roof Rating Council

I live in Pennsylvania and I have seen vinyl warp here. Not sure you have to be in extreme heat for dark paint to warp white vinyl.