Seeking advice as I'm looking to purchase a second home while holding onto my current townhouse in Chicago. I bought the place in 2020 & this winter I'm renting it to close family friends to move to Colorado for a few years. The plan is to purchase a townhouse in Denver, and in a few years, move back into the Chicago home and utilize the Denver property as a rental unit. My biggest concern is how to report this on my taxes, I want to make sure I have everything in order. Any tax advisor recs?

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We have a somewhat unique income structure between my self employed husband, me traditional w2, income from my family’s farm in another state and our rentals and my husband used turbo tax. Walks you through it all. Just keep documentation of everything, even open separate bank accounts or get specific credit cards to use for each property to keep expenses very visible and you’ll be fine.

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Make sure you take depreciation. On sale, that would be reduced from your basis whether you deducted it or not.

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