Gurus are just following their fulfillment companies play book its all based in MLM from decades past same presentations same tugging at heartstrings  exact same terminologies etc.

This can be done by using sites like AirDNA, or by clicking on Airbnb/VRBO and seeing what similar properties are renting for and how booked they are at what rates. 

How does their track record compare to their past forecasts.I highly suggest the book by @Brian Burke On passive investing 'The Hands Off investor"

@Deborah Wodell Please see  zillow history and Redfin history for that area and see if it improved in value over 10 years and then conclude whether it is worth to keep it as a rental or sell..Usually to become wealthy one should not sell Here is a great book for youhttps://www.coachcarson.com/building-wealth-one-house-time-j...

I plan to focus on short-term rentals in a property that I’m house-hacking, and hopefully move on to multifamily properties from there.I purchased Brandon Turner’s books Rental Property Investing and Investing in Real Estate with No Money Down.

Just make sure you do everything by the book and within the required timeframe.

(S)he should have access to a number of insurers and policy types.I checked with Proper and Steadily and both do not allow more than one booking in a house at the same time.I'm wondering if there are any other insurances that do allow it?

Make sure you get the latest edition of the book!

I have a property manager who helps with the booking and renter issues (if any), a cleaner who turns over the property.

Also could be a hybrid state.You might read the book 16% solution.