However, I think from a financial perspective, it's likely a better idea to pay off the debt or add the money either to a taxable brokerage account or a retirement vehicle like an IRA.

@Robb Almyfrom my perspective ... i don't really worry about 'price.' 

My HELOC lender does not allow electronic payments just checks, but because my contractors generally want straight cash or else electronic payment, I usually cash the checks myself and then send the payments electronically (which is not great from the perspective of my HELOC transaction history, since it looks like I was sending the money to myself only).Please help!

Any chance you have colleagues investing in the area who might be willing to share their experiences and perspective?  

I also manage STR's on Oahu so I have some perspective from that side. 

I have read many books and articles on the subject, but I'd like to hear some perspectives from others who have already started their investment journey: when you thought you were all prepared and put your plans into action, what unexpected and/or difficult issue(s) came up?

First thing I want to say is, I'm sorry that you have this perspective.

The factor that determines the state of this investment is more often than not the time horizon of the individual investor, your perspective is everything.

Re: Homeowners Insurance on a Real Estate Investment Property from a Lender’s Perspective
I am a private money lender.  Amongst other things I always instruct the insurance agent that the property will be vacant. I...

(And I've seen so many emails from agents trying to sell me on Granby Ranch for Airbnb and short-term rentals, I'd love to hear your perspective on it.)