Luckily the guest plays for the NFL and is going to pay but my client self insures and had no coverage. 

My wife and I purchased our first rental property here in Maui in June of 2023 to use as an STR as it was a consistent market, numbers worked, and we live 5 minutes away from the property so self-managing made sense! 

Thanks, yes I am self-managing.

I've got to go take care of some HUD tenants James, sorry I didn't answer the question to your satisfaction, I can imagine that must be frustrating for you to think that I have to do something to the level in which you require in order to be sufficient.

This is the IRS "intro":https://www.irs.gov/businesses/small-businesses-self-employe...and this is their 256-page guide to train their auditors:https://www.irs.gov/pub/irs-pdf/p5712.pdfSo yes, you will come across different opinions from different tax professionals.

We have perfect feedback and Premier Host, and allow Instant book, but do not have a liberal cancellation policy and have some rules in place (4 day minimums, for example) and are not fighting the cheapo battle, and we tend to get somewhat buried in the search rankings.One of the things that really burns my *** about VRBO is that they allow the property owner to self select the type of property that it is rather than forcing it into where it belongs.

Additionally, I am in the process of closing on a commercial property, which requires a $300K down payment by October 15.If I settle the tax bill, I won’t have sufficient funds for the property down payment. 

Talking JUST on normalized revenues, payroll self $5m annually......

This isn't including other expenses I know but I was planning to self manage the property and hope rates continue to go down so I could refi in the future and gain more margin in rental income.After further analysis and speaking with a friend thats a real estate agent I may want to shift my original plan and sell it.

It was hard work, dirty work, nobody liked doing it but, it was guaranteed work and $ to feed one's self and family.