Also, the home is located near the following: major freeway, hospitals and healthcare facilities, located within 15 mins of downtown, plenty of restaurant options nearby, etc.

If I owner occupied in b area or below I would consider this as an option.  

In fact, if your tenant does poorly, it may put you in a situation where selling is the best option and you will be stuck using the agent that caused the problem in the first place! 

I plan to hold this property towards retirement as it's in the area I grew up (obviously anything can change).I am receiving conflicting statements from contractors/friends/family on which roofing option to go with.

I've looked into a few options that won't cost 20%.

One option to consider is enrolling your property with ALE Solutions.

However, this is not applicable to standard M1-2 zones.Zoning Map Amendments: If the property is not in an MX district, pursuing a zoning map amendment to rezone the area to a district that permits residential use is an option.

There is not even a cohost option that I know of.Are you going to get a PM license?

I recommend a broker that works with over 220+ lenders so they have more options than just your one bank.

Will be glad to check options in more detail.