Honestly, that's sort of like saying you need to go back to school to learn about real estate --- what investor has done that...Looking back at your OP, if you haven't you might want to see what part of your "extroversion" doesn't fit your current job duties. 

To the OP, yes, usually when they toss around HUGE NUMBERS, it is a misdirection.

OP, you just need to get better at assessing the property’s condition during a showing.

As per your OP, you two are the owner/members of the LLC. 

Your OP mentioned insurance wouldn't cover?

While it's true that the points raised  by the OP are valid, many of the issues listed can be avoided.

OP said the water lien wasn't recorded when she took title. 

OP will need to buy out a tenant or wait the year to when the leases expire if they want to move into a unit. 

@Basit Siddiqi the OP just clarified their LLC is taxed as an S corp...which seems like that may be the clue for why this transaction may be taxed?

I wonder how many $M's of dollars the OP has invested in his own real estate empire, or is he (like most of the advice-offering "experts") offering advice with no real personal experience in the game.