Be sure to talk to a good accountant before any possible sale in order to make it as tax favorable as possible. 

Should I do both evaluations, and then choose the "best" one (in my favor) when making my offer?

One very passive investment strategy I favor these days and that is producing very nice returns involves investing in portfolios of 10 SFR at a time, co-owned with the managers.  

Later, as you get more experienced, you can return the favor and have folks help you.  

They are taxed separately, so I should be able to buy them as two quads (with favorable financing). 

I personally wouldn't evict, just make the fee structure more aggressively in your favor and help train him to pay earlier.

Being a Realtor, I am biased in favor or using a Realtor, but if you have a buyer in mind, you could get away with just using the attorney.I have been involved in many transactions over the years and have found that the "normal way" is the exception rather than the rule.

I think there are some positive things to come from the federal level with our Congressional delegation/F-35s coming to Fairbanks/Trump's plan for infrastructure spending/tax plan/more favorable towards business; but oil/gas/mining are what drive Alaska.

To Follow is Ga Supreme Court ruling>  Federal Home Loan Mortgage Corp vs City of Atlanta (no S08Q1846) (MArch 23, 2009) is a case heard in front of Ga Supreme Court and rendered a verdict in favor of FHLMA. 

This is how professional gamblers, playing games of skill (poker, 21, etc) can make a good living at it, despite the odds being in the house's favor.