To Sell or Not to Sell (to buy more properties of course)

[Michael Turner]

Ok, so.... When I first started investing a few years ago, not only did I lack most of the investment knowledge I have now, but I also lacked the ability to go to a bank and ask for a loan for an investment property. What did I do? I paid cash for most of the properties until I learned I could borrow against the appraised value of the properties

I then took out a loan through a hard money lender on four of my properties, and even lumped another property into the equation that I didn't own yet (a benefit of a hard money lender).

Fast forward to now, I have 3 mortgages, and 11 properties, all of which I've bought 100% either with cash up front or with the refi from others. 

I'm at a point where I could sell every property and, in a way, start fresh with the knowledge I have now.

Here's my thoughts:

I sell every property and come out with 1.4m - and that's after paying off my debt.

I then take the 1.4m and invest in multiple (larger) properties with multiple doors. Now my 11 properties are down to lets say 5, million dollar properties that I've only put 20% down on, and that will cash flow significantly more, all while still having a remaining 400k to use for fixing them up if need be or to invest elsewhere.

My problem lay in the logistics of it all... Not only will I need to ensure we 1031 properly and make sure we have some properties lined up, but I need to make sure banks will even work with me now that the only cash flow I have is my other business (an IT Support Company - an MSP). It cash flows well, but in this theoretical situation, I have now eliminated $7,893 of monthly cash flow from my property business.

I'm seeing $$$ signs and want the advice of the community to open my eyes up to some things I may not be seeing, or to say "hell yeah, sell 'em all!"