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Wellness Wednesday for November 1, 2023

The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:

  • Requests for advice and / or encouragement. On basically any topic and for any scale of problem.

  • Updates to let us know how you are doing. This provides valuable feedback on past advice / encouragement and will hopefully make people feel a little more motivated to follow through. If you want to be reminded to post your update, see the post titled 'update reminders', below.

  • Advice. This can be in response to a request for advice or just something that you think could be generally useful for many people here.

  • Encouragement. Probably best directed at specific users, but if you feel like just encouraging people in general I don't think anyone is going to object. I don't think I really need to say this, but just to be clear; encouragement should have a generally positive tone and not shame people (if people feel that shame might be an effective tool for motivating people, please discuss this so we can form a group consensus on how to use it rather than just trying it).

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Much better with the rewrite. It seems like a somewhat complicated situation. Since you're talking about the 2 in 5 rule, this implies that property A was your primary residence in the past - for at least 24 months of the last 5 years.

So you could sell both properties, and essentially choose which one to pay cap gains on. As only one property actually has capital gains, this is no problem.

It sounds like you've already fixed on selling property B (your current home).

As to Property A, you could sell within the next 1.5 years and avoid cap gains. But you're losing a 2.75% mortgage and good renters. Personally, it sounds like you have a good setup with this property, and you should just keep it. Rent will increase over time more quickly than your costs. And with depreciation, I assume the current rent income is mostly or entirely tax free.

When your tenants move out, you can 1031 exchange and avoid paying capital gains taxes. If you're lazy you can 1031 exchange into a triple net lease. This might be better than renting out your parent's lake house. The risks of renting to unknown people are pretty high in many jurisdictions right now.

Just my 0.02.