How I have it set up currently is the owners (my clients) are receiving Airbnb payouts and I send an invoice at the end of the month for my Mgmt fee.

For example, certain liens will not go away such as property tax liens, code enforcement liens, certain city liens, etc.  

I'd like to charge a per use fee to at least help recover the cost of repairs each year or buy new machines.

Also, will I continue to get the W-2 Tax benefits using the STR loophole if I move these properties into an LLC?

Do a tax loss harvest  4.  

To some capital, as long as the product is not traditional vertical, apartment-style product then it is still build for rent.The biggest evolution I have seen in Build for rent recently is the transition to multi-parcel and for sale/for rent hybrid developments which is contrary to what was more standard in build for rent 5 years ago---traditional single parcel developments for density and tax purposes.

This way you wouldn't need to provide paystubs, W-2s, tax returns etc. 

2) How much are you spending to get the deal compared to the average assignment fee?

I'd been thinking, "I should be able to handle this myself--but now I have to really study up and make sure I don't do anything wrong, cuz now this precious squatter is threatening me with legal action--AND I want to avoid lawyer's fees."

I've always thought Chicago had outrageous property taxes.