My dilemma has been that I've gotten a little behind on some revolving debt that selling this property now could eliminate in addition to giving me cash on hand to trade into some better value or start a new construction duplex project I've been wanting to start.

And I could use additional 200K or so to fund my next investment property. 

Many investors budget an additional 5%–10% of gross rental income for CapEx, though this too depends on the property’s condition and the age of major systems.

@Kevin Connauton most PMCs won't touch this type of renting due to all the additional headaches and liability.We second contacting PadSplit.

I currently have a homeowners plan with Allstate and plan on asking them if they have something like a short term rental rider plan that I can add in addition to my current plan.

Feel free to private message me with any additional questions.

After talking to support (who were actually quite responsive and helpful), they told me I had to publish the ad with only one photo first and then re-post the ad with additional photos later to force the first photo to be first.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

You''ll need more down and additional reserves.

Additionally you can always write in what was done to correct it and explain that since then you no longer had issues.