Jason, I don't disagree with your general advice on addressing common objections.

What to invest in depends on what your objectives are. 

Let's discuss your objectives.

The objective is to leverage both time and money.

I have personal experience with that and it wasn't fun.As a general guideline, a joint venture with more than 5-7 investors may become difficult to manage, particularly if there are multiple decision-makers with different ideas and objectives.

Because of that feature limitation, I ended up swapping them out for dumb irrigation controllers.As an experiment, one time I tried leaving a pre-configured wireless access point with a tenant specifically for smart smoke detectors and irrigation controller, but the tenant objected because it meant I could potentially access their network whenever I wanted, which was theoretically true (not that I would do it).

Their main objective is to find off-market properties for investors.

Came across your post and we just started to look ourselves with the same objective of possible STR and second getaway home.

"We'll just refinance it." coming from someone paid to originate your ARM might not be the most objective advice you'll ever hear.

Some yahoos like one of the dozen or so Yardi iterations, but I don't get those folks so I'll pretend it doesn't exist.There is a whole different class of PMSs like RentReady, TenantCloud, Hemlane, etc that CAN be used to do some or all the things you'd prefer, they just won't function AS well for as long as the pro-grade PMSs listed above.So, if this is a side hustle that you'll dabble in for a while and then hop onto the next shiny object that walks by, I'd go with the cheapest or best UX/UI you can find in the second group.IF this is a business that you intend to keep getting better at and pursue with excellence then I'd cut right to the pro-grade PMS and learn to use it masterfully.