If it is a personal residence, there is a chance that she will itemize instead of take the standard deduction.

Since I pay my contractor on a job by job basis, what I would like to do is assign these items to specific weeks they need to be done.

So if you have no LLC activity and you're going to file a Federal individual tax return what additional items would need to be reported for Federal tax purposes?

The IRS defines home acquisition interest (which you can take as an itemized deduction) for your first and secondary residences as debt used to buy or build a home, and should be secured by THAT qualified residence.

Then round upAverage kitchen makeover probably can be ball parked based (Then round up) on big item needs but I have no idea.As you can tell - I am very inexperienced so all this is just speculation but hopefully someone who has some more knowledge will see this and chime in!

Are there any other types of insurance or additional items the homeowner should add to their property insurance to deal with having roommates?

And the title insurance will only cover the items that it is required to cover.

If you can acquire a home warranty to cover major items that could insulate you.  

If the property is new or recently upgraded, that is, roof, HVAC, plumbing, electrical, the BIG cost items then number 1 is good. 

@Elizabeth GomezHaving an LLC without a business leaves no benefit.Having an LLC doesn't necessarily just make things like cell phone bill, gas deductible.Once you have a rental that is placed in service - you can benefit from being able to deduct items that relate to that business.