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?

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

I'm fresh.

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.

(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.)

Updated the bathrooms, fresh paint and updated light fixtures.

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...

Hello all, my name is Brian floyd and Im a fresh back into the real estate market since 2021. 

As I read once, try to have your business efforts be cumulative, so you are not always fresh on the learning curve, where the risk is highest.