With a WY LLC could you engage in the following real estate areas wholesaling, lending for commercial and/or residential business opportunities, short-term and long-term rentals? 

Financing for multiple family 5+ units is a completely different product from any residential loan and being able to quickly identify and engage the best option for a specific deal may be the difference between a successful closing and a lost opportunity. 

If he gets emotional, don't engage.

I'm thinking about engaging a real estate accountant for a more seasoned opinion, and a real estate attorney to think further ahead.

Luxury vinyl plank (LVP) is another option.

But at the very least you should start with an feasibility study on a specific piece of property and then engage a civil engineer and architect early on.

This thread is in the Canadian Real Estate Forum, which generally only engages investors from Canada.

I think you're going to either need to engage an attorney for review (best), build some non-attorney contacts who can comment on whether or not it seems customary (better), or just risk it (first, of course, trying to understand the full scope of the risk). 

I am also engaged, a first time home buyer, and I will be house-hacking.

In reviewing the legal docks leading up to the foreclosure, there were numerous attempts by the association attorney to contact HUD without success nor did HUD engage in legal avenues of their own.