Gable roof. The gambrel roof is really a gable roof with 2 differently pitched roof planes. A gable roof is usually the least expensive option as well.

Bell thanks for your clarification - I think your photos illustrate something I would say too - that we want to understand what the original design intention was back in 1905, not so that we can slavishly create exact replica of how it was then, but so that we can go out and choose products and furnishings that fit in and create a beautiful and cohesive whole. No reason at all modern pieces couldnnt fit in with the overall look and feel. In fact as we can see from the previous owner's efforts, trying too hard to look "historic" just left us with a cliched 1980s version "Victorian" which really wasnt very authentic and true to its origins at all. Similarly, I think it would be a mistake for OP to go out and fill the house with 2017 interpretations of "craftsman" because the end result would just be a 2017 interpretation of craftsman. One of the best kitchens I saw in an early 1900s house (wish I could find the pic) used a mixture of modern and vintage pieces. It was unfitted, having freestanding pieces, worktables, and a kind of utilitarian industrial feel that was quite modern, but in its way far more authentic to the house than a lot of the ubiquitous white fitted cabinets + granit counters you see on Houzzz. Guess Im so interested in this thread because my house is of the same era and very similar style - ie has strong arts and crafts features but floorplan is your basic midwestern Wisconsin foursquare vs the classic Chicago bugalow. My approach was basically to strip it down to its essentials - remove 100 years of GACK - all the layers of flooring and wallpaper - so exciting to find the original paint colors (all golds, browns, grays, bronzy greens, one room was a dark inky blue that Ive become quite fond of.) I wont do exactly the same colors but finding them did get me to rethink my color scheme. I do have some arts and crafts oak pieces (incl a massive oak library table in the kitchen now used as a worktable) but also mixed it up with other fav and well loved stuff, vintage up into the present. Oh one other thing to acknowledge is that OP's house is part of a historic tour, so Im guessing she will probably want to be leaning in the direction of being more faithful to historic roots than some of us are. Still, that doesnt mean it she cant freshen it up and make it hers.

At some point in time, cheap "updated/modern" window were installed. Possibly around the same time as the aluminum siding. Just intalling architecturally appropriate sized windows with muntins will restore the colonial character to the facade. This house below reminds me a lot of yours. I grew up a couple towns over from Marblehead, MA. The section of Marblehead known as Old Town reminds me of what your house could be. Here's a site with some pictures of houses in that area: https://historicipswich.org/2016/02/03/colonial_marblehead/

We would like to remodel the whole house room by room as we enjoy doing most of the work ourselves. Refinishing the wood floors is on my list after my toddler exits the hell on wheels stage. I don't believe the tile is under the kitchen cabinets, I definitely want to change the kitchen layout. The roof, living room windows, and kitchen appliances are damaged and need replaced this year. I also need to replace all the bathroom sinks because they are not kid friendly. I'm considering putting in more substantial baseboards as the current ones seem very cheap compared to the crown. I agree with updating all the lighting and adding updates through furniture and decor for now. Thank you all for the advice! It helps to have outside opinions.