I purchased my original home many years ago when I was single. It is a very small condo unit and was much cheaper than I could get a "regular" house for at the time. Later I got married and purchased a larger home, but let a family member (parent) stay in the old one. They have been living there more than five years, but now they are moving out and I want to sell it. My family has gotten larger and is running out of space and also needs a larger home than the one we have now, and with the sale of both houses we could potentially afford a larger house. However, it seems tax laws have changed since I first moved and now there are capital gains tax on sales of a second home which may jeopardize that as home prices have gone up a lot and so all the gains from both properties would likely be eaten up by a higher price tag on a new home.
Are there any loopholes under which I would not have to pay this tax? Something like if I roll the proceeds of both sales into a new primary residence? Or maybe due to a family member having lived there?