So basically I'm at risk of the tenant damaging my property and not having a way of going after her because she is not signed to the lease. 

In the past basic zoning pretty much allowed you to rent a house to 2 unrelated people (family/kids obviously don't count as they are related to the adult(s). 

Basically do the work above and beyond what the average flipper is doing and you will find/get the deals before they do.  

It sounds like you have the basic 20/25yr 3tab shingles, which yes are prone to "flip up" or break off, esp as they get older.Find another local Roofer, that for sure taunts that they do Repairs, will warranty their work, and get the repairs done. 

Basically only NE Jackson has owner occ activity Sojac very little to none anymore all investors who are only going to pay for what ever the cash flow is and deduct for risk.

(I’m still trying to understand the basics!) 

So many don't understand basic economics. 

In other words, if you buy with true cash (meaning not hard money, no lien was put on the property at purchase, etc), then you can get a mortgage for up to six months after closing based on the purchase scenario (basically a cashout refi). 

Hi Jazmin - While TurboTax can handle basic rental income, a CPA would add insight, especially for a first-time rental with mixed uses like yours and even explore tax strategies tailored specific to you.

It's a good location but an overwhelming rehab just beyond my experience; sorta a full gut/ or the basic kitchen, bath, flooring and paint remodel.