(You’re protecting equity/your net worth, if you don’t have anything you don’t need an umbrella.)I used USLI for a long time but they changed their standards a couple years ago and wouldn’t offer more than $1-2m if any property had a pool.

I just sold my business and in looking for ways to offset capital gains taxes stumbled across a strategy in which a STR can write off all depreciation in year one via a cost segregation analysis, thereby reducing taxable income greatly for a specific year.

Using the LLC asset only makes more sense to me, but I've heard it from tax attorneys for example that the appraised value is what's used each year, until The Person owns 100%, then it's game over.If anyone has direct knowledge or first hand experience or can point me to a specific reference document (IRS perhaps?)

I am hoping some short term rental owners and possibly locally to you will chime in and offer any information for you.

At this point he has not offered me any deals just dollar for dollar value exchange when the work is done. 

To my point, that is a very specific type of investing, and obviously the worst of it is being shown for entertainment. 

If you have specific questions about property management, I'll be happy to help! 

I don't really have enough information from you to give you very specific advice, but I can say that if there is any room in the rent, it's probably only a couple of dollars PSF which isn't going to drastically change your overall monthly nut to crack.

Do you have specific criteria or a particular investing strategy you’d like to explore?

I offered them $250 cash to be out by March 15th if they paid what was owed for this month and last month.