Our “new” house was built in 1994 - with Hardie Board siding (before their very specific install instructions) and Milgard vinyl windows - so everything was very good in 1994 but is past it’s lifespan now. With the exception of the wood edge trim, the Hardie is in fairly decent looking condition except for two problem areas with paint peeling - next to vent hood exhaust and above AC unit. The house needs some serious caulking around the windows ( siding installed before z flashing was required) as the state of the current caulk is allowing water to cause problems - not sure how long that’s been going on - probably a while.

The windows need to be replaced - several are foggy & don’t shut well anymore. The caulk around the glazing is oozing out and the low e coating seems to be doing nothing at this point. We got a quote for $30k to replace the windows with exactly what’s there now… 25 windows - many very large. They would have to cut the siding and add trim (none currently) around the windows to do so.

We also got quotes for painting the exterior $10k and $20k - I suspect a fair price is more like $15k.

We could also just get the vinyl windows reglazed and replace the glass where needed for 1/2 the price. Some windows are probably too large for someone to want to touch so we’d be stuck with those. We could remove and replace the bad portions of the siding and get everything painted. We get a lot of direct sun and sideways rain - suspect a paint job won’t last 10 years no matter how good.

I’m wondering if we should caulk the windows and wait… save up to replace all of the siding at the same time. Based on the water issues I don’t feel good about the house wrap / window flashing. Maybe we could also evict the attic flies who hibernate under the siding on the west side. I’m also not a fan of the way the lap siding and shingles were combined on the exterior - the house is awkwardly shaped and they made it look worse.

Does the prefinished Hardie with the 15 year color warranty make it worth it (added bonus of not having painters around for a while)? Is it insane to think about replacing the siding if only some of it is begging to be replaced? Does replacing the windows at the same time offer cost efficiencies? Has anyone bought a house in a similar state & what did you do?