Turning the management of the rental over to a property manager can relive a lot of these issues.

Quote from @Neeta Agrawal: For context, we gave the tenant a 60-day notice for non upkeep and no repair communication in 2023 and then extended it for 30 days upon his realtor's request, setting the move-out for May 31, 2023.

But you have to ask proactively, and be mindful of how long you stay in forbearance to avoid long-term credit issues.🔹 Insurance Challenges – Even when insurance pays, it rarely covers the actual cost to completely rebuild.

I don't anticipate any issues, but you never know.

Continually communicate clearly with all parties involved to make sure that expectations are as close to realistic timelines as possible.

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

Communicating timelines and expectations upfront can help prevent losing good prospects to other properties.I'd say it's a potential red flag if they want to sign the lease without viewing it.

And, the best you have given is that you want $4k because they didn't communicate to you in a timely manner?

They may also be able to temporarily relocate your tenant to avoid any other issues.

This is a very common issue in parts of Milwaukee and I have done lots of basement reinforcing on our rentals.