I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

I own a roofing company in Denver and a separate gutter company there too. 

Type of construction materials for the build(block/metal frame/wood frame), separate utilities, finishes, tech, cleaning crews, any tips and tricks would be HUGE! 

I have a separate short term rental insurance policy (insurance agent recommended short term policy over long term since it's ultimately being used as a short term rental) Curious if that is the same as the Airbnb $1M liability insurance or if they have a separate one

You can simply request a separate check for the $100 increase to bring the total deposit in line with the new rent amount.

I can also send you a separate message on where to find other meetups as well.

Question 2: Is it a good idea to put every piece of property into a separate LLC entity (1 for 1) or is it okay to put a few properties into the same LLC?

Perhaps we "buy" the house from them for the $328K balance to satisfy the lender and don't need a large down payment and then have a separate contract with them to pay $x per month until we've paid the full $172K amount.

The reason you see a person’s name and all their entities listed in a lawsuit is because Plaintiff (the suing party) attorneys have to list everyone and every entity that can be remotely tied to a cause of action, otherwise, if enough time passes and through the legal process discover that a separate entity or just a person was truly liable and they didn’t name them in the lawsuit, they are out of luck.

It also requires different reporting of that separate interest expense on the K-1 each year so the partners know they have the obligation of tracing that interest expense to however the partner used the distributed proceeds.I typed all this up and realized Mr Brooks has left the building and posted this 6 months ago, but hopefully someone else will find this useful!