I work countless hours night and day and my sleep is pretty much non existent. 

i couldn't sleep at night a few nights ago so i was just on here posting.  

For all those that work a full time job to pay the bills (I feel you, RE is my part time job for nights and weekends but has quickly morphed to a full time job and i'm sleeping like 4-6 hrs a night), keep fighting!

Which one will sleep better at night?

Its almost 3am and I cant sleep but obviously my brain its at its peak right now.  

We seldom actually sleep in the unit.  

I mean, you can do that too, but it's always nice to have where you live paid off cash, if for no other reason than it allows you to sleep incredibly well at night!

I am currently thinking about sleeping in the detached garage & converting it to a live-able space or sleeping in an office space converted to a bedroom on the first floor.

I don't think I would sleep at night knowing I'm upside down on a few of the properties I own and having staying power is important to me.

With regars to long terms buy and hold, all cash holding would keep you sleep better at night, however cash on cash return would be less than leveraged investment.So if i have cash and a good w2, i would buy all cash, then wait for seasoning time then refinance, then repeat..Kevin