Remember a true STR under the tax rules isn’t considered a real property trade or business.

Ultimately it’s personal preference but if you choose to proceed without permits you should at least use trades who have the ability to obtain permits in Philadelphia.

Hi @Jessica Heller I have lots of different trades & handyman available. 

For example, stock trading became more widespread with the advent of online brokerages.

That is in real demand here for people in the trades.   

One bedroom (the master) and the upstairs bathroom, have no heat whatsoever though so space heaters have been used for them in the past.

just a couple things:-you can house hack and not deal with tenants directly as @William Collins notes. you just hire a property manager. it will cost more, but that's the trade off.

You should also look into Sold properties to see what househack deals are actually trading for.All the best!

Warren Buffett didn't get rich by day trading.

It depends on if you got to the level of a trade or busienss which would determine if its ordinary income or not.Then the amount of time you spend on the business would determine if its passive or non-passive.