We always use a smartlock, at least one outdoor camera over the entrance, and a noise monitor inside. 

If you haven't seen a tax bill at your higher income bracket, you might want to get a colleague prescribe something first (joking).The warning: Any kind of "hands-off" approach will require you to diligently monitor the operator.

No different from any other contractual provision.To date, I've heard of only a very few lenders who even put forth the expense to monitor such things: BofA and their acquisitions being among those very few.

The tenant is asking us to pay for the security system and monitoring.

Quote from @Sheryl Sitman: Thanks for sharing.Finding a good property manager is a lot like finding a good Tenant: you need to know what a good one looks like, check many to see if they meet your requirements, select one, regularly monitor them to keep them on track.Many investors hire the first one - or the cheapest one - they can find, then complain that Property Managers are terrible.

Do we invest in a monitored alarm system for the property and pay for it ourselves? 

Please be very watchful and closely monitor your contractor, and don’t forget to call references.  

This means that you will always need a minimum of 10% down to cover seller's closing costs.If you're talking about larger multi's that require commercial financing, that's another story entirely.You should absolutely be monitoring the MLS to get a sense of the market and there are deals on it.  

One strategy we use is to ask for a higher rent than the estimated rent and then monitor the showing traffic.

Monitor the progress, and make sure you exit as you planned.