Why not paint the wood siding you have? That old growth pine will outlast the vinyl and allow you to repaint when trends change.

You have an attractive American Vernacular style
house.
Please consider Hallets suggestion to paint the siding.Soft greens will evoke a story book look,especially if you use white trim.
Does this house have double front doors?If so that is another factor to decide on.
The porch looks in good shape,choose the stain you prefer.
Have you thought of widening the narrow path and opening up the entrance steps?
Of course ,plantings of flowering bushes and various perennials will also enhance the charm.
Best wishes for an eyecatching lovely transformation.

When you choose a new color for siding, consider how the house will look in winter when surrounded by snow. The sunlight will be much weaker than in summer.

A contrast with gray snowy and rainy skies could be done with chambray blue, barn red, butter yellow, or sage green.

What's important is how you want to see it welcoming you when you drive up to it- do you want quiet blending in with surroundings, a cheery brighter color, a classic color with white trim?

I agree the wood siding painted so much better choice that vinyl . I love the sage with white trim on that house

This has so much potential! Is there a reason you can’t paint?

Have you already tested for lead in the paint? Kits run about $15 from amazon or big box stores. Results in 30 seconds.

I have a 100 yo house with the original siding (painted many times). I'd paint. If you like greenish gray, go for it, but paint the trim white or cream, depending on whether the paint is warm or cool toned.

Pay a lot of attention to the false positive rate on lead tests. Some can have very high false postive rates. The result being if they show no lead, you can be sure there's no lead, but if they show a postive result for lead, you can't be at all sure you actually do have lead.

So we had fire recently in my neighborhood and the vinyl siding just melted and added fuel to the flames. It is made out of oil and oil burns hot.

I am also reminded of my realtor saying after we had looked at an older home with new vinyl siding, “It’s like wrapping a corpse in plastic and not expecting it to decay.”

So really, paint that gorgeous old wood!

Having a house that was built in 1901, I know that while a freshly painted old home looks great, it also is a lot of maintence and is very difficult to get the primer/paint to adhere to the old wood. We have tried a hundred (maybe not a hundred) ways to paint to get it to adhere longer without much success. We wished that we had put new siding on it a long time ago, because painting a house is costly and time consuming even if you do it yourself. So do your research and then decide what works for you. I like your color choices.

I see both sides of the house siding dilemma. But my suggestion to paint rather than side really comes down to the window trim.

YOUR WINDOW TRIM IS FABULOUS! Can't say it enough. love it. remember that when you put vinyl siding up against existing window trim, you loose the profile. a channel is necessary to hold the vinyl siding in place, it just changes the look.

@Lyn Nielson, that's a very good point too. Hard decision.

Hi everyone thank you all for the suggestions!! We were not able to paint because all the previous paint was lead positive and lots of wood rot that needed repair.