I purchase the home at a substantial discount.

Most houses in the Poconos don’t even have Memorial Day weekend booked, which is typically a huge weekend and typically books up well in advance.

My goal is to house hack my first home purchase.

It was in my neighborhood so I was familiar with the area and the prices of homes coming up.

They aren't licensed or insured.At least a PM is typically licensed and insured.From what I've heard Joshua Tree is very saturated so it sounds like your doing good to break even.Since you seem to be doing everything right and going beyond what many are doing, adding someone else to manage the property will just lower your Net profits from having to pay them.

We typically use Price Labs, and our team will tweak our weekly rates to make try to get booked during the week.

The homestay is an owner-occupied STR in which you basically rent out a part of your home while you live in it.

I wouldn't limit it to roof as wind and water can damage other areas of the home..what if a window was left open and the interior now has water damage etc...Did you already bind your insurance (likely not if you are two weeks out) So there may not be a reason for them to dictate you get it reinspected. 

I rented out my condo (short term - midterm) to move in with him, and now he is ready to rent out his single family home (long term).  

It will most likely trigger the due on sale clause in a standard 2nd home mortgage so read the fine print.You can always use a commercial loan instead.