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The cost of upgrades is prohibitive. It would probably cost us 20% of the home's value to really upgrade it to a reasonable place. Replacing our oil boiler with a heat pump based central air or mini-split system will cost us almost $40k -- 4x more than a simple oil boiler replacement.

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Indeed. A lot of it is the failing of the government to offer meaty incentives/subsidies for these upgrades. Unfortunately the US still doesn't take climate change seriously or they'd do more than pay lip service to green initiatives. They'd actually incentive people to put in double pane windows or heat pumps or ceiling fans. I'm not even talking about urbanism and city design here, just help the existing renters and owners of SFHs in the US.

It's a lot of money but it's a matter of perspective and situation whether it's prohibitive. If energy/emissions are more expensive, the upgrade would pay for itself sooner rather than later; other countries have generous financing aids; you buy a house assuming that there'll be expenses like that in the upcoming decades (and planning the money correspondingly), ...

Yup, we need to be careful not to beggar current residents or create more resentment toward environmental initiatives. Offer subsidies in the beginning, and after a while, simply begin to tax electricity along with its pollution effects; price in the externalities. But we're a _long_ way from doing that in the US. We can't even get people to take the train from a park-and-ride to work and back!

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