Be extra careful that what you're seeing here is in fact what is going on!

One of their contractors requested an extra $100k.

that is a lot of bathrooms to clean and if you have a maid an extra expense.

Would you take the guarantee or go for the extra $100 a month? 

They were getting free food, shelter, and even cell phones!!

I'm thinking you could do it if you were to lease the extra beds in your primary, plus your existing rental, plus a 600-700k luxury airbnb (10% down second home loan), plus an additional luxury airbnb purchased with conventional financing (20% down) and using the same operating systems as the first purchase.

Of course, if you think you're going to spend that extra money on "hookers and blow", as my friend @Jim K. would say, then you should probably leave it in the property. 

An extra $25-50 per month and you want to upgrade something in exchange. 

For example, is it an extra bedroom or bathroom? 

If you live in an extra unit you often can not have a stove or regular sink, but many people pull the stove for inspection and the put it back, but there may be an insurance issue there.