It's time to start investing!

[Russ Schlehuber]

Hi, I signed up a while back but have not been active. This is really my first time looking around and I'm brand new to real estate investing. I've purchased and sold homes in the past but all as primary residences. I'm in a position to start heavily investing and intend on becoming very active. I'm hoping to build my knowledge in how real estate investing can help me shelter my taxable income from my occupation and how to best build my portfolio from the ground up. 

I am both a licensed Real Estate broker and Mortgage broker so I have the tools and foundation to make this easier. I am located in Michigan.

My first question as a member: I currently own my primary residence free & clear and have owned it for over 3 years. I made an impulse decision to purchase another home as my primary using 100% VA Financing and convert my current residence to a rental. I have my loan application in hand but am second guessing my decision. Yesterday, I both completed my taxes and put my loan application together. After realizing how much I paid in taxes last year I'm thinking that there may be an additional tax benefit by putting the mortgage on my current residence and asking the seller of the place i'm buying to do a land contract with a 60% down payment. Is it better to have no or little mortgage on my primary while taking out a mortgage on my current house that I am converting to a rental? I'm also concerned about losing capital gains benefit if I convert my home to a rental. If I need this money for a future down payment on another primary in a couple of years will I now have to pay capital gains when selling it in 2 or 3 years after it's been an investment property?

Thanks for taking me in and i'm excited to become a large contributor to Bigger Pockets!