As a seller, financing can make you a lot more money, but gives you risk.

I’m thinking about selling one of my debt free rentals to pay off the loan of the new house – thus erasing the $3500/month loan payment.

You can run the risk of using it as a short-term rental, but doing so is a violation of the loan documents you sign at closing.

Thanks.just a side note, the tenant has requested first month free rental, windows coverings (not satisfied with the new blinds being provided), and free utilities for 5 days.

You don’t have to necessarily retire with debt-free assets.

All the free rental software, like the one I use, hold the money for 4 to 5 days like you said.

Just a little nervous on the risks and collateral depending on what lane I take loan wise etc.

Yes, feel free to shoot me a message.

You are taking the risk of not making enough to cover the rent so due diligence is important.  

Being from Canada, I'm doing the same but I'm targeting short-term rentals as they are much more profitable and justify the hassle and risk of going overseas.A low interest rate doesn't make a good deal in and of itself.