Having all these units in one property also provides you with fantastic efficiencies as far as insurance, maintenance, etc. 

The market is too efficient to let that happen unless there is more to the story. 

Did a live in flip and added efficiency/mother-in-law suite for $14,000 cash in.

They are more tax efficient, more liquid and cheaper.

If you have any intent on renting a portion of your residence that you're moving into, part of your new home could be considered 1031 but only the portion that is rented.Depending on the amount of equity you hold in your current two properties, it may be more tax efficient to do some sort of HELOC or cash out refinance to acquire the new property you will move into.You should also note that there is no capital gain exclusion for selling the investment property (except a 1031 which is temporary) but selling your personal residence using section 121 automatically excludes $250k (500k if married) of capital gain.If those avenues are not possible, you may be stuck with the capital gain tax.

Having checkbook control is far more efficient in terms of paperwork, time, and money. 

Being more efficient with expenses, finding creative ways to make $$, hustling harder, working smarter, etc.

We completely redesigned the space and made 1100 ft.² highly efficient and BoHo chic!

How “hands on” do you have to be, or is that handled/managed efficiently through a PM?

The most tax efficient way to handle dividends is to pay them back into the policy.