There's plenty of people flouting the rules, but I don't recommend it -- at any time they could address their housing shortage by cracking down on STR heavily. 

We do need to polish up on our sailing skills though, we're not quite as skilled as our friends, but we could probably get there. 

I wouldn't trust them to make the payments, especially if the property value goes down and they have a bum tenant not paying rent because they mis-managed it and had poor underwriting skills to begin with and realize they messed up and just walk away (what makes it attractive to them if it's not attractive to you?).

Time, skill, hustle.Become invaluable to the community around where you know the person.

We have a chronic housing shortage, which results in an extremely hot rental market, but it also makes buying very competitive.

That sentence makes me question their drafting skills.

They key differentiator here is their English skills since you also want them to make calls, that's the first thing you need to focus on. 

As a skilled negotiator, listen attentively and ask the right questions.

Maybe money is tight, maybe it is the summer and people are feeling more inspired to make the recurring Home Depot runs, or maybe people are taking more initiative to round their skills on Youtube University. 

@Erwin McClain how will software go beyond enhancing your DIY management skills and actually replace a PMC?