Frankly I think too many people try and "automate" everything with technology that they complicate things so much that it is hard to manage.Remember you will get older folks staying and they might not want to try and use a tablet.I agree with Michael. 

Once comfortable with an investment, start investing (not the whole ball of wax), but 20% or so into an area and see if it is really fits the personality and desires.  

However, you can be more comfortable with your offer if you can have your GCs do a walkthrough and provide total rehab estimate prior to making your offer.

In my opinion, you should hone in on what asset class you're comfortable with and just focus on that.

The roofing company want to rent the house and will do all of the renovations while staying in the house, as workers from their company will be staying there. 

It is in an enclosed gate area that can only be opened from inside the fence so I'm leaning away from using it as storage space while I have other guests staying there.

Get out of your comfort zone.

I don’t know why we didn’t get that vital piece of info in our initial meeting.So my wife and I are extremely relieved .She says she will stay on as a courtesy and if things come up it will just be an “ hourly “ rate for emergency type situations or basic boots on the ground necessities.We really like her enthusiasm and positivity and she is great at communicating and seems  sincerely empathetic to our situation.

Second since I am a property owner myself and also own a PM company I try to look at it from different angles.If the tenant wants things fixed it many times means that they plan to stay in the property and since they are picky they tend to take care of the home more.

I wouldn't necessarily put a lot of efforts into improving/building/spending in hopes of staying booked solid, but it is a nice 'side hustle' for a pretty piece of land to bring in some extra income while it sits.