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. 

Of course, I totally understand that you wouldn't want to do if that guide is written by another real estate agency, in which case you have option 2.b.

She is renting the apartment, not the entire property.It's very important for landlords to understand Landlord-Tenant rights and maintain control of the property.

I understand that it gives you more coverage and it better if you are transfering RE from someone that you don't know... but in my case I will be transferring from myself to my LLC.Some good answers here: https://www.youtube.com/watch?

Seek to get an understanding of what they know about ADA compliant (probably nothing), present your case in calm friendly manner.  

Before finalizing anything, I wanted to get a better understanding of how to evaluate different real estate opportunities and what challenges might be posed. 

I understand that it is less than ideal, but it is reality. 

I am hoping to learn more about how investors analyze their deals and make decisions, as well as looking to better understand general real estate investing.

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

Is there some other way to verify his involvement?