@Megan Mason recommend you watch some of the videos from @James Wise youtube channel on S8 evictions.We've been dealing with S8 tenants for over 20 years and they are NOT a cure-all for rent collection challenges.Since rents in Class A & B areas exceed S8 limits, most of your S8 rentals are going to be in Class C/D areas. 

It just helps... limit your liability to that property.

This would be ideal in terms of cash flow (after a few years) and equity appreciation since you'd be achieving tremendous returns on limited equity in the form of appreciation, principal paydown and tax benefits aside from only cash flow. 

I commonly hear that permitting is not an issue unless I am touching plumbing or electrical but just to be safe and avoid any future liabilities, I am trying to understand it is even feasible to get the new rooms/garage permitted for their intended use.3.

If, after the first ten (10) days after you take possession of the Rental Unit, it becomes necessary for us to undergo including, without limitation, prevention and remediation in your Rental Unit and/or on the Premises, you will be held financially responsible for reasonable costs thereof, paid as Additional Rent.

While it can be beneficial for spreading tax liability and estate planning, DSTs are complex, costly, and subject to IRS scrutiny, requiring precise implementation.

This allows you to postpone tax liability until you sell the new property without a subsequent exchange.2.

I currently have 25 accommodations on Hospitable, but it's starting to be limiting for the reasons you must have encountered.I'm currently looking into Guesty and Hostaway, and I'm having a hard time making a decision!

Entities are primarily used for protection from liability.  

Investing as a limited partner/ passive investor is a somewhat risky endeavor whether it in private placement or in the public markets.