Along with the professionals you trust to help make these decisions (CPA, Attorney, Financial Planner, Insurance Agent, what have you.)

However, to make real profit, I buy using Subject To and sell on Lease Option which I explain at https://www.biggerpockets.com/forums/311/topics/1141313-subj...While it isn't "no money down" it is still reachable for people who are planners, who think ahead and who are committed to real estate investing. 

Maybe I should team up with a couple wedding planners if I decided to do it?

I am renting to party planners.

Anyone know of a good tax planner or CPA that I can best figure out my plan going forward. 

I currently work in downtown Chicago, consulting as an urban designer and planner.

I am someone that can produce value in some of those areas as I am a florida licensed real estate agent, a licensed CPA, as a Personal Financial Planner as well as being a nationally certified business valuator and a Nationally certified forensic accountant.

@Chris VairBefore you get all exited about a possibility, talk to the city planner or zoning department and rental license people if any. 

Talk to a financial planner first.

I am not a financial professional and offer you no professional advice whatsoever.I can say You need to take some action to protect your assets that will be left behind.You need to locate a good CPA and a certified financial planner to help you prepare your wife in the case of untimely death.I personally believe you should be looking into buying sufficient life insurance that will payoff the balances of at least half of your holdings if not all of them,whatever you can afford to pay but,that’s what you need professional advice about.