Nonetheless, I am still treating this very seriously as if it was not family.

If you can't get one or two closed within the time then treat them as separate exchanges and use the 3 you could bunch to purchase a larger building.   

We are both educators and teachers at heart and really want to take care of people the way we want to be treated.

@Brandon PomerantzThere is flexibility when taking out retirement funds as a result of the cares act.You can pro-rate the income over 3 years.You can treat it as a loan instead of a distribution.One potential negative is that if you consider taking it out as a distribution it would be taxed at both federal and state tax rates.If you have rentals now and the distribution will put you above $150,000, you may lose being able to deduct the rentals against other income.It is hard to say yes/no to it being a good idea.

In theory, the mortgage should be in the LLC's name and the LLC would report the income and expenses it has.Since this is a single member LLC, it will be treated as a disregarded entity unless you elect to be taxed as a corporation.

Learning first hand how poorly some people treat their tenants and their property.    

It’s also important to remember, as soon as you turn the keys over to your new tenants, they won’t treat the house the same way you probably do.

We are both educators and teachers at heart and really want to take care of people the way we want to be treated.

An additional risk I might add is treating your STR as just a real estate investment instead of what it-a hospitality business.

Just treat REI like everything else you've done and you'll be okay.