Can I still expense it or does that create some issue?

and my fiancee and I are looking to create about $5,000 a month in passive income, so that I can afford to work less and we can travel together during the summers (which he has off).I'm thinking that I should begin by house hacking since we are currently paying 2,000/mo in rent.  

The strategy sounds fine but will be a slower process (time) as well as more expense with your cash being tied up inside each property.I'm a fan of the  BRRRR method, where you use debt to create assets and then have the renter pay your debt off over time.

As others have said, I don't think this is a big deal, and you sort of created the issue by letting tenants know where you live. 

And if there’s $75K worth of rehab the owners annual expenses are likely artificially low, which is likely what created the $75K need in the first place.

It would be much more simple to do steps 1-4 than to legally create a loan. 

There is a lack of land to develop new homes which create scarcity. 

So I am currently creating a pitch for my company to open up the ability to rent a room / house instead of putting employees up at local hotels.

Listening to the BP podcasts, they are constantly urging you to create relationships with local banks.

I took it several times and used the concepts that I had trouble with to create flash cards and reviewed those over and over.