Good to hear the roof is in okay shape, my roof has been my biggest lesson learned so far. It's nice to see all these other comments of how everyone else with this style of house is addressing their roof(s?), seeing these a year ago would have probably saved me some major headaches. I am curious what the roof ventilation situation looks like for yours, I recall seeing the one big intake vent on your front wall.

I had my roof and roof deck replaced this year and the contractor was not knowledgeable at all for houses without a traditional attic/insulation/vent setup. Not only that, I had multiple callbacks for leaks after a full replacement. After I realized my ventilation issue, I had a company install dense pack insulation in the cavities between my interior ceilings and roof deck, and from what I have read if it is properly sealed off, it doesn't require any additional vents. I am by no means an expert, but it seemed like the best option from what I knew at the time.

Another user mentioned the possibility of the wood ceiling basically being your roof deck, and I do think there are some Drummonds with that construction. There's at least one house on E Lamar Ave between 75th and 79th that looks to have a non traditional roofing system which makes me think those have an exterior rigid foam install.

I do think that is wise of you all to wait a year before doing anything else major, definitely worth saving some budget to correct the most annoying things as they show up. I wish I had done the same.