Hi Davin,You will want to word it as a deposit instead of 1st or last month's rent, because a tenant could interpret that as they don't need to pay you last month's rent.Each state allows different deposits upfront, check in the area of your rental. 

Ask strangers on the internet to interpret every paragraph of a legal contract for you then rely on their answers to determine whether or not to execute?

Is there any legal/accounting interpretation/loophole which would allow for that sale to be considered a "capital gain" so that I can utilize my stock losses as an offset?

Many months ago I sent questions to my state's AG office and I am happy with the state (NC that is) Commissioner of Banks providing the interpretation.

I was aware of what you outlined and that there was guidance after it that clarified the interpretation, but I wanted to be sure nothing changed after 2019.https://www.biggerpockets.com/... 

An Administrative Interpretation is recommended for a building where a short-term rental will be located.

Let me know if I interpreted your comment correctly.

Assuming the source website is legit, the tax law can be interpreted that if you only own a few properties and it's in your name (or an LLC and you and/or your spouse are the sole member) then you do not operate a trade or business and are not required to issue a 1099 regardless of >< $600.http://landlordsolutionsinc.com/2013/12/does-your-handyman-need-to-fill-out-a-1099/However, I did read on this BiggerPockets post: http://www.biggerpockets.com/forums/51/topics/87325-issue-w9-for-work--600... that it's generally a good idea, good practice.

The proposed HUD Rules interpreting the federal SAFE mortgage act can be viewed at www.regulations.gov Use the search parameter "HUD" and the keyword "safe".

If you PM me I can give you my interpretation of it, but that isn't legal advice.