To complicate it a bit more, I’ll add that we were also contemplating doing a flip as our first deal, then switched to the house hack idea, and now are going back and forth on which might be better to start.

Little more complicated, but once I'm educated on the topic and understand it well, perhaps it's a great option.

Purchase price: $355,000 Cash invested: $100,000 Contributors:Might as well do a complicated deal for your first one.

I also understand the costs associated with the property transfer from a person to LLC, as well as potential tax complications.

Unlike many other appliances, the plumbing is less complicated than some things as the drain water is pumped through a flexible hose to the existing sink drain.

So it can be more complicated than just a contractor buying a house to flip themselves. 

Why complicate your life by combining those into more problems?  

It certainly would be less complicated doing 2yr increments.

(PPP etc) If they have, perhaps you should be getting your rent or at least a piece of it.This is a complicated issue but communication between both parties is very important and you probably want to talk to an attorney who is done this kind of thing before ie. 2008.

For complicated tracking and scheduling I use Trello.