You just described our mountain home (well it is a 1970s fixer...). Depends on the condition of the windows and siding - we did windows first because the existing windows were in bad shape and it would get very cold in winter and hot in summer. We put storm doors on too at that time. Then, we did the siding (replaced it with stucco actually). Then we saved up, and are just getting started on the bathroom and kitchen gut job.

But if you are in a more temperate area it would be good to at least get your plans in place for the kitchen layout, for Emily's reasons. Our only regret with with how we ordered things is that, along with windows and storm door we replaced the garage door, and now 4 years later we are converting that garage to living space and the perfectly good garage door is getting ripped out :(

It's like a puzzle and there is no perfect answer! The important thing is to just start, and plug along. Good luck!

One important thing to remember is that it is always better to make the envelope safe and dry, and make sure you have good plumbing, and that your electric is all updated. All the pretty stuff, should be last. Pretty is what you will enjoy the most, of course, but, the pretty wont last, if the house isnt water tight, and safe. I know someone here, that just redid their kitchen. Its beautiful (or at least it was), but, they should have done the roof, because, it sprung a leak, and wrecked the kitchen ceiling and parts of one wall, and now they have the kitchen torn apart again.

Thanks to all for your input, really appreciate your comments. Roof has two layers and HVAC is in attic. Makes sense to get these done together - both need to be replaced sooner rather than later. I liked, "make the envelope safe and dry". For the sake of the budget we will not be changing kitchen and bathroom layouts, Just chomping at the bit to redo those baths and that kitchen!! New windows and siding will have energy benefits. It will take years off this ole girl and return her to a state of beauty. You have helped very much! Roof/HVAC, then windows and siding, inside update 3rd.

If the only reason for the windows and siding is to save money/NOT because they are failing, I’d put them at the end after the kitchen/bathroom updates that will enhance your every day living.

They are both things to do only if you are staying in the house long term based on cost, too. Unless they are failing, only cosmetic. And- honestly most new windows don’t pay for themselves before they fail unless the previous window is failing, so it’s more of a comfort thing as well as cosmetic. Which is valid- but spend a summer and a winter before you decide. :)

We just did the siding on ours, which was in fact failing, but we did the kitchen and many inside spaces first. I don’t regret it at all- we monitored the failures to be sure they were not inside the envelope first, and then did it it cash once we’d save enough. Ridiculously expensive stuff, honestly. 😹

There’s no way the energy benefits of my $25k in siding will come back to me in heating costs. ;)

Windows can be restored, and properly cared for siding doesn’t ever need replacing, so I’m really questioning this list of yours and where it came from. Restore the windows, scrape and paint the siding. Maybe add storm windows. That’s far cheaper with just as good results. Thats a good curb appeal personalization that will help the home feel like yours.

A 2 layer roof will need a tear off to the deck, when it fails, with new underlayment and shingles or metal. With ridge vents and soffit vents added at the same time. That’s when you address the attic insulation levels and add baffles so the soffit vents work. Butcannintact roof can last 30 years, so the timing for that depends on how old that roof is.

HVAC replacement should occur after the roof and insulation levels are done. And after you restore and new storm windows. All of the above will help to tighten up the air infiltration and improve the HVAC’s response, making a smaller cheaper system possible. HVAC can also last 30 years, so again, age and condition factor into the timeline. Take care of it, and hopefully it can wait until last.

The rest is cosmetic rather than structural and systematic, and not really needed in order to comfortably occupy the house.

zennifer, yes, windows and siding currently good enough - not failing. Mostly a cosmetic change. Two windows will be reconfirgured when replacements are done. This home is long term investment. New windows in previous remodel did decrease our monthly heat/cooling bill by half, but totally see where you are coming from.

Verbo, such good info. Made me see roof/insulation project more completely so the HVAC is more effecient. The roof and HVAC made it to my list because of home inspection. Were told they both had maybe 5 years left, been in house for 2 years now. I did paint the siding last year. Would rather be proactive in addressing these issues head-on. The fails always seem to come at the worst of times! This house is in Oregon - cold, wet, damp winters. Have to be able to be comfortable indoors,