If it's a long-term play, the potential savings on PMI with a conventional loan could be significant.Have you compared rates for both options?

I’d recommend keeping the funds separate for each property to avoid any potential co-mingling issues.

Nothing in the STR space is one size fits all, but the ideas can help others see the potential in their property. 

These systems are becoming more sophisticated and (my favorite) capable, leading to improved user experiences and potentially freeing up human employees to handle more complex tasks and interactions.

Not sure why that happen, however the best way to screen a potential tenant is to see how they have performed in the past. 

This approach will help minimize the potential financial risks associated with renovations and working with contractors.

It's affordable and offers strong cash flow potential.

What are the potential pitfalls and benefits of each approach?

A quick fix now can save you from potential negative feedback later on.I'd be happy to discuss more ideas!

If your'e looking for purely long term appreciation you will likely do great in these markets but if you're looking to have high cash flow and avoid a potential major pricing downturn.