"You will be taking 2/3's of my income (never mind anything so trivial as math) and leaving me with a rental house backing up to a highway.

Check with a local independent commercial insurance agent that handles benefits, they will have a pretty good idea of the options open to you as a business.When we've done the math, a higher deductible plan usually wins out vs. higher premiums/lower deductible (especially if you can use an HSA).  

Both sides were occupied and had several months left on their lease.The two sides combined brought in 2600 a month (1400 one side, 1200 the other) so I did the math and with my down payment the mortgage / ins / taxes would be ~1500 a month.

Just do the math.

I think it will still be even quicker because you don't have to do any math yourself. 

You are on your way to finding a deal.Make sure that you understand the math on what is a good deal.  

The math supposingly worked out before I buy them .

Replacing carpet is about $600 per room so do the math on how much it could cost and how much security deposit you have. 

A large number of people's monthly bills are now just as much if not more than their 2 month bills now- and the company refuses to change to system or explain how that math works out.

If you are trying to save yourself the cost of commission for a buy or sell end, you need to do the math and make sure you are actually saving yourself money.