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> That also means if they sold it right now at that $20k "loss" then they effectively paid $333/month plus upkeep to live somewhere for 5 years!

This also ignores the costs in buying/selling, including agent fees, lawyers, etc. You should probably only buy if you plan on living in a single place for at least a decade.

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Unless you are willing to enter into some kind of a special arrangement, closing costs are almost always negotiated and usually paid by the seller.

That isn't true. States levy taxes and buyers brokers are a thing in some states, and in some cases they're less fully paid by seller (less than the customary 2.5-3, leaving buyer to provide 1 or 1.5). Closing costs include mortgage costs, too.

I've only ever heard of that stuff paid by seller if seller was a sponsor, and the market was a down market. Think new build in 2020 or in a depressed housing market today.

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