You also bring along a locksmith to change the locks.

We hired a locksmith to open it for us and at first everything looks okay, mostly cosmetic, until we went to the kitchen.

I ended up having an expensive locksmith do the job. 

As to the locks being changed you need to get a lock smith they can make a key and you can enter as soon as it's legal.

As a child growing up with mom and pop landlord, I reminded him that my siblings and I spent countless days and nights doing our homework, rehabbing,  getting up to go to school the next day, cleaning up after tenants, fixing faucets, unclogging toilets, calling locksmiths, getting ready for HUD inspections, collecting rent, writing receipts, and leaving with the check or cash payments (along with the receipt book in the basket at the front of my bike) and going to court with my Dad to threaten evictions.

I'd inform him, if he doesn't grant access to your friend/handyman at a specific time and day that a locksmith will be on call, the locks will be changed at his expense.

So I had to call the locksmith to tell them to get someone out to fix it.Can your proposed automated property management system do that?

Locksmith (I believe from WA) didn't like his reviews.

I would make sure you have the locksmith there on day one and lock the place down.

(give or take).Make sure you also factor in property management fees (even if doing it yourself), lawn care, snow removal, locksmithing after tenant move outs, landscaping and common area cleaning.