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. 

So many don't understand basic economics. 

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

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.

A property manager handles the day-to-day tasks, freeing up your time to focus on other areas of your life or business.

I've personally managed a number of house hacks, and the challenge is basically, you're dealing with a much more transient and unreliable tenant base than with other types of properties.  

Beyond these details, I’m excited to dive back into the basics and beyond—open houses, expired listings, online marketing, and more.

There are items required by law and in general those are related to the safety and basic comfort of living.