I have questions or clarifications regarding their income and student loans but not sure if I am allowed to ask them in more details about this if that could cause a discrimination type of claim or not.Tenant has deferred payments on students loans and said they could prove 3x income yet their bank statement did not show me that.  

Quote from @Nina Diehl: Typically this is something on the landlord unless there is something in the lease that states putting anything other than toilet paper down the toilet that causes an issue will be on the tenant.

It seems like an avoidable mess that is causing unnecessary distressPerhaps someone should point out that they don't own any of the rentals yet as they still belong to the dad. 

However, the thought of going into debt to start this adventure has caused my wife to not see my dream.

Our concern is further damage being done after we take ownership and before the squatters are removed, like something catastrophic is our main concern.

My main concern is that logically, it would seem that most of the bookings would only happen on the weekends, and less demand on the weekdays.   

I’m all for minimizing taxes paid but I have also seen lots of people get themselves all “balled up” in complicated structures that can cause problems down the road.I can tell you as a single man I sold my house in San Carlos CA back in 2014 so I only got $250,000 tax exempt.

There were a couple of comments/concerns regarding the individual LLC Operating Agreements, and you certainly want to have the Operating Agreements reviewed to make sure there is nothing in there that might cause concern or problems between each of the individual owners, but the most important document would be a newly drafted Tenant-In-Common Agreement that governs how the TIC will be managed/operated. 

Morgan It's hard to answer that plainly, but the fact that one of your main concerns is DTI in the future - you should be calculating the either cash flow or total interest you'd be paying with each loan to determine if the risk/reward is there for you.

@Mohamed Omer pretty vague intro, but here's some info we hope you find useful:The Real Estate Crash of 2008-2010 caused real estate prices to crash across the country - but didn't affect rent amounts.