If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

Or maybe they aren't confused at all and know that the path of least resistance for them is for you to bring the extra cash to closing so they do not have to have an uncomfortable conversation with the buyers side. 

Later, you might qualify for a mortgage from a bank - following the usual routine of an appraisal and meeting the loan qualifications of income, etc.

The loud music has stopped, but very uncomfortable to have a renter that ignores me and is hostile because I asked her a simple request. 

All three companies stated it is impossible to cause this type of damage simply with routine mowing. 

But, any legit business is used to routinely filling out W-9’s and it is no issue.

I routinely work with numerous organizations that have a 1000 or more corporate vehicles including LLCs where sequestration of liability makes perfect sense given the relative active business risks which are enormous and the relative costs of establishing and maintaining the structure are negligible.So again I say show me a small real estate operator that has been saved by an expensive and cumbersome legal entity structure that couldn't have been done it at least as effectively and much more efficiently through fundamental risk mitigation practices which disciplines one to act responsibly from the outset.In other words, running what are essentially passive real estate activities by retaining competent and professional management and a modest amount of insurance coverage (which should effectively limit risk sourced to the RE activity), and if you need additional coverage (for risk sourced outside the RE) get some ultra affordable umbrella coverage.Now I realize you won't be able to able to strut down the street pretending you are a player because you have an LLC, but it seems to be a very very small price to pay for not being played for a fool wearing the LLC trappings of a clown.

And I do not want to buy properties in my market that I would feel uncomfortable living in myself!

If you don't hit this threshhold, deductions allocated/apportioned to that unit would only be allowed to the extent of rental income.Painting and that type of work is typically (emphasis on typically, the tangible property regs are a good read) considered routine maintenance and is deductible.

I am actually uncomfortable answering any of your questions.