I'm looking for some advice on how many analytical scenarios I should consider and which scenarios should hold the most weight. 

It doesn't hurt and definitely helps shed some liability for anyone entering the property.

I couldn't get it all in one trip anyway (too much weight for a pickup truck) but the store is 10 minutes from the property anyway.

Wish you all the best and hope this helped shed some light. 

When I left the home, the shed had no power running to it but it was wired for power at a later time if i choose to (switches, lights, outlets).

And some fiberglass or,  better, rockwool insulation to fill up weight cavities in old sash windows.I know the salesman who came out and carefully measured your windows before giving you a quote offered you a careful spiel about thousands of dollars of possible leakage and damage and insurance and a bunch of other vague warnings.

After you rehab, I would put a weight and breed restriction on tenants with dogs.

Maybe she's gained some weight has a thyroid problem, or anxiety because she never saved money.

If you're running more than two units, have at least two small window units on hand at all times in your basement or a shed.

There are 2 names that come to mind that I think would be able to shed some light on this topic and be of great help to you, @Dmitriy Fomichenko and @Brian Eastman both have great knowledge in this area and can probably open your eyes to some great options for you.