If I am not entitled to the money by law is there any harm in asking him for the security deposit and pro-rated amount of rent for the month that was being charged or having my tenants nicely ask for their deposit and/or pro-rated rent back for the month they had already paid in advance?

Rules are being interpreted differently from municipality to municipality and some places have their own COVID rules so I'd talk to your local eviction attorney.In the last three months we've been able to evict a handful of residents WITH leases, two because they were breaking the law and threatening other residents with bodily harm, and a few more simply because they were not paying but had the ability to pay. 

What would be the harm in seeing how high/low maintenance they are before dishing out 5-10% for a property manager? 

If they are ok with the structure and you hold up your end of the bargain, then no harm no foul as I see it.

Court system is back open but having them leave quietly without harm to the property is your best bet.

Based on what you wrote above, if you're thinking of selling in 3-5 years and are price conscious, there's no harm in selling now because there's no crystal ball.

If it’s a great deal or you have no other deals to pursue it’s not really harming you.

Since you or the "investor" here is being harmed for Pat's nonperformance, specific performance would be an equitable remedy.... albeit an extremely long and frustrating one.

I have had many give me negative information, knowing full well it would harm the likelihood of them loosing a trouble tenant.

But, good luck anyway - no harm in asking.