I know its expensive but you will be well protected :)Or you save a lot of money and be better protected by doing this consistently and well:-carry appropriate types and amounts of insurance-sign contracts with indemnification provisions- obtain all necessary licenses and permits to operate your business-ensure all vendors/contractors are licensed and insured and list you as additional insured-sign well drafted and fair leases and be a responsive landlord -be an active owner or hire an active PM  who avoids or at worse timely eliminates premises liability exposure The strategies you often read about are sold by alarmist asset protection companies who fail to disclose how impractical they are.

Hired contractors for the heavy stuff. 

We are less susceptible to economic down turns because everyone here is a GS-15 married to a Booz Allen contractor and they will keep getting paid by the government regardless of what happens in the real economy.

What is the STR registration process with the City (I couldn't find any info)? 

Analyze properties using deal calculators and build a small team with a reliable real estate agent, contractor, and lender familiar with the Philly market.Good luck!

This team consists of an Investor Focused Agent, Lender, Contractor, and PM.Read this article on the "core 4".

Poor management of contractors, permit delays, or running out of funds can extend the rehab timeline, costing you money.

Hello, I own a plumbing company with 40 + employees and mostly work under contractors that do remodel, new construction and commercial work.

There are loopholes in tax laws but the entire system isn't a loophole.Again, here is the definition - Loophole- A way of avoiding or escaping a cost or legal burden that would otherwise apply by means of an omission or ambiguity in the wording of a contract or law.

Plus you will need to carry your own team or be in good with sub contractors which means you need volume.