It sounds like you are missing a conversation with the tenant to understand the situation.

Maybe it can help you in your specific situation, it depends.

But because he raised rents each year, and rents were increasing by ridiculous rates, tenants constantly moved, had to sell the property at a loss several years later due to constant vacancies.Finally, the most interesting situation I ran across was a tenant, a 93 year old tenant paying rent on a 2BR apartment for $90/month.

@Sawyer Smith, you mentioned that you’d be running the fund yourself.. it reminds me of a situation my cuosin found himself in a while back.

So you may not NEED a lease signed for your primary residence already, especially since that's a lot of stress to find a new tenant and have a lease in place while you're under contract on another home.

If you sold it, what would you do with the money and how does the return compare to what you get now (factoring in the amount of work/stress with each option)?

He is a smart dog and I think he could read the situation well.

Also, running a flip with no money and hoping you get a good return with all the other stuff going on in the background starts to add stress, and you end up not enjoying it.

Here’s a detailed look at our situation and the questions we have:1.

Don't ask on this thread, as most tax strategies require a good understanding of your current and future tax situation first.