Hi, Our door has been in only about 2 1/2 years (though this winter and last have had lots of extremes) and they look good as new. No refinishing yet. We have the easy to re-finish finish, based on our door-man's advice. We (I, mostly) waited 30 years to pick our entry way. I could not decide. When the house next door (built as an exact mirror of ours, over 150 years ago) was gutted, the entry was lovely so I went to the same folks to do ours basically the exact same way (though we did make a few minor changes). I do know how difficult making the decisions are. And, the design has no glass in the door but glass sidelights. We live right in the city. And I think the vast majority of our neighbors have glass in their entry way. BTW, is that huge opening in the front of your house for a garage?

Please don't pressure wash wood siding unless you like to see splinters flying in the air. As soft and spongey as that is, that is not a good idea. New siding with a factory applied color might be, highly recommended. Had a family next door pressure wash their deck which the previous owners had applied some of that 'great gel stain' tooo...mildewy now, gel stain ed by sap from trees above, etc etc........pressure washer....wallah.....holes in deck floor. Do NOT force water into your wood siding/sub walls/etc. You really might need some consult specialist in this case, but I do not see why painting this would help it for more than a couple of years. New siding, would be the most effective use of dollars and labor, you might check into this and see. Anytime you have a wood of this age, there is just the sense it has served its' purpose. I don't know what people put on homes like this other than wood, but NEW WOOD siding at minimum would seem the best cure for the problems. Have others experienced different results? Curious to hear from others with similar aged homes.

Back when home building ( 1920 ) made some sense in the four season climates, you had an air lock, a vestibule. with a second entry door, and it was many times glass. It's purpose wasn't to protect your flooring it was to protect the inefficient, less even heat and save you from a blast of icy cold air. The floor was brick.......tile, slate. It was a contained space. We no longer have that nice little contained space. If we did? We'd not use it. Neighbors don't knock on front doors when out for a walk anymore. Folks like Beth above? Common for it not even to get opened! We go in and out of garages attached to the house. In wide open spaces as today, where a "foyer" is in name only, that? ONE surface please? Wood and a rug solve the rain, snow dirt.........and ........ the tile just breaks the space, and makes the rug harder to find. So you can COVER it. Kinda dumb in my book : ) Like the loss of air lock vestibules.

Regarding the shutters - it's not the color of the shutters - it's that the windows are too wide. Shutters are supposed to look functional even if they aren't functional. They are supposed to look like they can cover the window on which they are placed. They never go on bay windows or triple windows unless they are Bahama type shutters which would be inappropriate for your area and inappropriate for your house. Please read this short article on shutters: https://www.lifeofanarchitect.com/residential-architecture-101-shutters/ As to the front door, that oval window is what makes it a Victorian style door. Your house isn't Victorian and would look so much better with an MCM type door or a solid door. The reason others are suggesting a light color for your door is that a brown door creates the "black hole" effect on the face of your house. It's hard to visualize if you are accustomed to seeing the brown, brown, brown that you currently show. There are other neutral, but lighter paints so your front door becomes visible. I agree that the landscaping you have now buries the house and doesn't bring out it's features. I hope you end up with a good landscape plan. Reach out to the landscape forum here too. They can provide suggestions, for free, to enhance your landscaping.