Besides your CPA you might also benefit from a professional tax planner and money manager.

Is one of you a long term planner and the other makes decisions on the fly? 

This arrangement would cause use to miss out on the long term vacation planners but also there might be a premium we could charge by being a short notice STR, much like airline charge more for tickets closer to the day of travel. 

First thing to do is see what the zoning says re the "burn down" clause, where the zoning code/planner tell you whether one or both structures could be rebuilt if destroyed. 

And continue to highly suspicious of the central planners and financial engineers.what is in my portfolio?

@Justin HrochBecause seller-financed deals can pose tax complications, engage a financial planner or tax expert as part of your team.

Do they have a lender, insurance agent, financial planner and attorney who say they are wonderful partners to work with?

Can anyone make a good recommendation on a real estate lawyer, business lawyer, estate planner or CPA in the Hampton roads area?

I can also give you a referral on a property management company. http://www.forbes.com/sites/erincarlyle/2016/01/27...http://www.forbes.com/sites/ingowinzer/2016/07/29/...http://www.crainsdetroit.com/article/20150607/NEWS/306079987/planners-seek-to-make-grand-rapids-medical-mile-a-healthy-place-tohttp://fox17online.com/2015/03/17/grand-rapids-rental-vacancy-rates-lowest-in-country/http://mibiz.com/item/22318-grand-rapids-said-to-have-lowest-rental-vacancy-in-the-countryhttp://www.michigan.org/blog/guest-blogger/three-reasons-why-grand-rapids-is-beer-city-usa/

Find a certified financial planner (e.g.