@Patrick Philip there is a lot of legal jargon in them to keep you and him completely safe.

Some risks I saw come to reality: increasing condo fee, board threatening to pass rental restrictions on units, including on existing landlords/owners.

Real estate agents have NO CLUE as to what is correct and legal!!!

What are optimal times I should call, and are there certain legal restrictions I need to be aware of?

This is completely legal and has withstood many court cases.

We owned a 2 bed 1 bath that we purchased in 2006 and shortly after buying it we learned from the city records that the 200 SF bonus room was not a legal addition and the walls were basically poorly mortared cinder block on a concrete floor that was covered up with drywall to make it appear like a finished space.

Hello TomA lot of the rooms on craigslist that I've seen over the years have lots of restrictions and rules which can make it difficult to find a tenant for a room.

The senior lender will want a subordination agreement and may impose restrictions on repayment.

I don't think that applies here based on the records I have found so far, but I'll definitely keep that in mind as one of those weird edge cases to try to understand better if I end up getting deeper into this process.3) you call the IRS lien department they can fax you a paper document stating if there is a lien or not its best to have this - unsure about the 120 days start date but we can safely assume it starts once the sale occurs or the date its switched legally in the clerk systems.Maybe calling the IRS will be a bit more enjoyable when it's to talk about someone else's taxes? 

Personally, I would like to legally avoid as much tax as possible.