I am happy to share with you how I accomplish this and even throw a few potentials your way.

As a general strategy, is it poor form to throw in a low ball offer or place an offer with the intention of finding something wrong that will allow you to retrade the deal (i know this is questionable)?

I see a lot of returns where depreciation is calculated incorrectly - Just throwing that out there as it may help to have it reviewed prior to reporting in case there are any changes to depreciation that may save you money. 

Doing it wrong at best leaves her kids involved and worst throws it into probate against her debts.

If you would throw in some Small Multifamily Units in the picture, you can not only have better income per door, but also achieve financial freedom and critical mass in less number of transactions.  

Many certificates expire worthless at the 7 year mark when people who bought a certificate on a junker property realize they’ll be throwing good money after bad.

One little falter on your part can throw the tenant back into the TESTING PHASE.

@Steve O'Keefe Looks like you've made a decision on what to do, but I wanted to throw my two cents in.

I installed big windows in each room, did tape n bed, texture, trim (with panels), AND INSTALLED 12MM LAMINATE FLOOR, all for only 3k in labor cost (I was honestly broke and low priced hoping he would throw me bonus money at the end).

Capital improvements should be an expense of the land owner as part of a lease option, otherwise you risk throwing that money away if you do not exercise the option.If the Seller's big concern is taxes go with a straight Seller Financing arrangement as it will provide the same outcome.