There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

Like you, I’m diving into books and podcasts, but I also believe there’s immense value in learning alongside others and gaining hands-on experience.I’m in the process of connecting with like-minded individuals to create a community of new investors who are eager to learn, share knowledge, and even collaborate on deals.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

Your risk vs. reward is way off balance there. 

I'm never in favor of government over stepping, but I can also see how desperate individuals can be taken advantage of during this tragedy. 

Use caution when borrowing against your stock portfolio, especially if it's a high volatility portfolio comprised of individual companies.

If he didn't want it or can't afford it, I would have reward him with 60 days time to find another place, then find a new tenant that can pay what it is worth….  

Personally, I airbnb half of my house, individual rooms, and stay nearly 100% booked.

The entire goal is to help you / individuals like you who are interested in a finding an agent who works with real estate investors.

I can't tell if you want to buy land from an owner who finances or if you have the funds to buy and then sell the lots with you being the owner who is financing to individual lot purchasers?