It just seems like there will be many that fail to file their report and I just can't see the government really going after tiny businesses for so much money for something that is so easy to forget to do.

I e filed claims with both VRBO and AirBNB and had no issues having them paid.

If I invest a multifamily through a Roth IRA, will I still receive the same tax benefits as I would with personal cash when I file my tax return?

It's typical and recommended one tax professional handles the entire filing.

Same goes for number of LLCs and what to fund them with, since bear in mind that CA tends to be more cumbersome and expensive to have LLCs than other states.California is generally more cumbersome than other states when it comes to taxes and filings.

I use Proper, but have not had to file a claim yet. 

@Terris Elliott It is very easy to file the articles of organization and obtain an EIN.

You would not be able to exclude it from your DTI until you filed with it on taxes (assuming you did so and did not report a loss). 

For me, I had to file in both FL and CT and pay annually in both FL and CT.  

I am trying to see if anyone can attest to their service when filing a claim.