Mine are letting me know if anything is broken and needs to be replaced, when items are low and need to be restocked, and if she is running late for the next guest check in.

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Normally for rental upgrades, I seek a 24 month payback.

I have thought about purchasing a 3/2+ SFH as a primary residence with the intent of renting when we are ready to upgrade.

You have to ask yourself if it's worth it,financially.Probate is not cheap and your share of the proceeds will be sharply reduced with all the attorney and court fees.Plus,the original lawyer will want money for defending the estate from the lawsuit (whatever the reason for the suit).It could take a year or two to fight the sister and in the end,the lawyers will eat up the money from the estate over time.Unless the house is worth at least $200,000 or more as is without major repairs and upgrades needed,I would seriously question whether fighting the druggie Aunt is worth 2 years of litigation and court appearances.It is just my opinion as someone who has suffered through probate,don't take it for the gospel.

You may want to make some upgrades that you know will set your unit apart from other units in your area, like granite counters, to allow you to charge a higher rent.

Ensure the bids are broken down by trade at least and ask questions about how the fee is built in. 

His shop was recently broken into by a sub that felt he deserved to be paid but did not finish the work properly.

Here's a general rule of thumb:If it is to bring it back to good condition, it's a repair & maintenance expense.If it is to improve, upgrade, or somehow make it better than the original, then it's a capital expenditure.I suspect most turnover expenses are repairs.

Before deciding to upgrade anything (vs making it serviceable) you need to know the specific market and what would be expected in those properties.