There are numerous ways to do it. 

There are numerous packages available.

The people lending you the money will have done numerous deals.  

https://www.amazon.com/Westcott-Stainless-Office-6-Inch-10414/dp/B0015ZY25IThey made a movie about your insurance company, here's a link you might enjoy:  https://www.youtube.com/watch?

And still almost 4 month since then, I have asked Nomad numerous times for anything that would help me understand the new tiers and how its different from previous division of responsibilities. 

You ever seen the movie "Yes man"?

Hot tubs, pool tables, movie rooms, kayaks and canoes, bikes, games, nice comfortable beds, smart TV's, video games, well stocked kitchens, etc.

Our private covered dock and lake toys are a bug draw for us in the summer months.Multiple people have said they love the pool table.In our bigger cabin people like the large game room, movie room, custom covered firepit and hot tub.

There were at least 4 maybe 5 individuals on Dave’s team that handled numerous things like; getting any necessary info from me and the title company, providing my account statement (proof of funds) for the sellers of my replacement, working with ERG for the exchange documents I needed to sign for both closings, and getting the 45-day form filled out and sent back to ERG.

Is that less desirable than a property with 5 bedrooms with walls, but less convertible entertaining space that could be used for movies, gaming,etc?