Please post a pic of your entire front view of the house from the front.

Are you considering these changes for appeal or because you have to replace the cedar siding you have now?

here's the front. mostly looking for low maintenance and curb appeal

You don't have enough roof overhang for board and batten. Are you considering vinyl an upgrade?

not enough roof overhang will affect board and batten siding specifically? mostly considering vinyl as a low maintenance option

I have my doubts. i like the curb appeal. it's why I bought the house. the cedar has seen better days. I'd almost have to rip it off and start over. there's some water damage. But it's not an awful mess. I'm trying to think ahead

I agree with Ryan. You have the distinctive elements of a Storybook house and with the cedar shake it is much less maintenance. To me, it looks like someone either changed the front door from the true arched storybook door to a regular rectangular shape or it was never installed from the beginning. Look to the roots of your home and restore/improve what you have since what you have is a true treasure. Here is the type of home with the door that would go with your style. Here are a couple of examples, you don't have to go with the hole in the door, but the rounded top is what I had in mind. It would help bring your home toward the more classic storybook elevation

Also, remove those shutters from your windows. They aren't sized right and those particular windows are too large.

Here is one that isn't nearly as exaggerated as the two pics above, but has some of the distinctive elements...

Agreed, custom rounded front door, shutters off, keep the cedar shakes and add beautiful light fixtures on both sides of the front door and improve the front landscaping. Awesome house!

OP, you do have an awesome house, it just needs a little bit of love right now.

agreed. I like the round door idea. I can see that. what do you mean about the size of the shutters? ha I've been working on the landscaping. not seen in the pics I posted

Here is a brief article about shutters and where they belong and do not belong. There is another article that goes into more information, but you will get the idea when you read this one.

https://www.lifeofanarchitect.com/residential-architecture-101-shutters/

A couple of links for you about storybook homes

https://www.houzz.com/magazine/12-storybook-cottage-gardens-stsetivw-vs~68863913

https://www.houzz.com/magazine/how-to-design-a-storybook-cottage-stsetivw-vs~24787402

https://www.houzz.com/magazine/11-real-life-gingerbread-houses-stsetivw-vs~5850890

Does this plan match yours?

yes pretty close. I think the 2d floor storage is part of my master bedroom

You might have a Sterling Kit Home. Sterling was in Bay City Michigan. The plan is from a 1945 catalog.

Wow ppf...what a great find.

my house was built in 1951. and I'm in western ny

A competent carpenter (very rare) could very easily weave in new shakes in to replace rotted or damaged ones.

I agree with what has been said. Your house is adorable! I have to ask, where is that overhanging tree ? I cannot see any trunk. It seems that it should be trimmed back. Is it hanging right over your house?

The cedar shakes on your house are lovely. In an ideal world, you should keep them. That is if there are no woodpeckers in your area, and no insects, and no hot sun drying out and splitting the shakes.

But realistically, cedar needs regular maintenance and sometimes it's ok to let it go and replace it. Certainteed makes some nice products that look quite nice. There are also PVC shakes made by nucedar and Royal Celect. Perhaps start by contacting a few contractors for estimates and they can give you the address of homes that have the product you like installed. Good luck.

Wood siding is endlessly repairable, and you can repair just the affected sections. In ten--20 years when the vinyl gets brittle and cracked it all has to come off and get replaced.

Thanks for your feedback!

The Sears Maplewood model has a similar front (roofline doesn't match like the Sterling home posted above) and the catalog drawing shows shutters on the front.

The Maplewood

Look at cement board or cement shingles not vinyl