They do appear to have steady bookings each weekend still.I would love advice on getting funding.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

You should learn to read the report and decipher what it's telling you.Here's a detailed guide on how to screen applicants: Application Screening Guide 

I’m eager to invest opportunistically into real estate and so I’ve been immersing myself in real estate knowledge through books, podcasts and videos, which led me to the BP community of supporters.

We just installed an AI text & dialing system which can handle real phone conversations and book meetings into a calendar.

- and finally once you do this, realize it will never even be close to how it actually plays out in real life, but it can serve as a guide for what sort of money you may need to save up to try and actually accomplish something like this.

It does not matter if they have house-hacked or not.Milwaukee has more duplxes than any other city in the US (including our friends in Chicago) and by default we sell a lot of dupxes, so I could probably write a book about house hacking, but the best advice I can give you is stop looking at listings and start interviewing agents.

This requires a minimum of TWO booked and completed stays, one is not enough, as was tested in court.

If you wanna tell me a little about:Your goalsYour capitalYour credit ratingI can help guide you where to start, what kind of project may be right for you, suggest some markets to look, offer you some sample terms on a loan.  

I never read the book you referenced but at least it appears the book is written by a tax professional which is a good start.