If she's not communicating with the potential buyers to raise their offers and with you about which offer is better (which is clearly the one that gives you more money, so unless the house is selling for more than $1.4 million, the first one) then fire her and/or complain to her broker.Now maybe she's new at this and deserves the benefit of the doubt.

So if she's planning on selling the house before 10 years have gone by and using the capital gains to pay for living expenses, OR if she's still in her 60s and can reasonably expect to need the cash flow for more than 10 years, it could be nice to have that ~$400 bump in cash flow in 10 years while forgoing the $100 a month for the next ten years. 

You are in the right place to gain the knowledge to build an empire.

Curious as to how everyone evaluates the true benefit of a property, to include the benefit of depreciation, etc based upon tax bracket etc. 

.  :(  At the time, we thought that was a smart move to basically defer our gains/short term income in the interest of having a paid off property in 10 years.  

Also if you run other businesses, a different structure might be more helpful.Currently, seeing that the corporate tax rate was lowered significantly, depending on how much profit you want to reinvest in the business, an actual corporation may have some benefits as well.I'll say that generally an S-Corp would be the way to go, but there may be situations that make a corporation tempting.Be sure to work with a CPA that knows your specific situation.

However we are wondering what, if any, tax benefits may arise from putting both of our wives on (or leaving them off) and splitting things in 25% increments?  

If you want to live in the house and title it in your name you get tax benefits upon sale (if occupied 2 years as your primary residence 250K if single and 500K if married) gains are tax exempt.

However, with all the knowledge I gained I'm still hesitant to get my feet wet.

Suddenly the unsafe reputation they had gained vanished when the buildings were rehabbed and people began to pay more to live there.