Goosehead (because of their lax onboarding standards) does not get the pick of the litter when it comes to carrier appointments and they've caused significant issues with profitability at many of the carriers they do have relationships with. 

You are going to have "seasoning" issues trying to take cash out.

The Management Company is recommending at this point, because there is a dispute, to send some kind of bill showing that this work was done and if not, it would be best to issue a refund.

Just wondering what the implications are of changing a single member LLC to a multiple member LLC as far as current depreciation, basis, carry forward losses and any other issues. 

I understand for tax purposes that I can only take two-thirds of the expenses related to the house to offset the rental income.

Zoning should not be too much of an issues, but uses may alter parking requirements. 

There's a ton of information available on these forums if you're ever unsure about anything, take a look around, chances are another person has encountered the same issues and share their experiences on here.

I-if it's "big expense", I get ahead of this issue by whipping out a receipt book (you can buy one at any store like Target, Wal-Mart, Staples, Office Depot, etc) and jot down the work that was performed, materials, hours, amount of people, other expenses, etc.

If so, would this still cause issue with the S-Corp tax rules?

By showing the full 1099 income on the return, it helps mitigate the risk of IRS flags or inquiries related to unreported income.However, it's worth noting that the IRS typically matches 1099 income reported by payers to the income reported on taxpayers' returns.