Does it have shared systems you have to manage or separate utilities for everyone? 

If no one but owner-occupants can STR... then that should mean opportunity for owner-occupants who STR their primary residences in many jurisdictions.- Large remodels or construction projects (Live in Flip) can be self-managed, worked on directly, and the value add, after 2 years, is largely tax free up to certain limits. - Many areas around the country allow for ADU Construction - house-hackers enjoy similar benefits to remodeling projects by being naturally on-site for ADU construction. 

*Any red flags unique to the Pittsburgh market.I’m also hoping to connect with fellow investors, agents, or property managers who are familiar with the local market.

I invest, flip, and own a property management company in CT. 

BLM  ( bureau  of land management) 3.

Capacity and Tolerance. 1) Capacity: how many people can you comfortably fit in the property, is there room to add more, or add more value to the tenants to increase rent.2) Tolerance: How many people are you comfortable living with, if there are vacancies are you able to handle that.House hacking is an amazing path to homeownership, and a nice low barrier to entry into self managing your properties.

Especially if you are hiring property management.

Not a rookie - While I have never purchased a home without an agent, I have purchased two homes in the last fifteen years in Denver and, at some point, managed both with some form of rental income, plus helping my mom manage the independent basement apartment in her home.

How much are you having to pay the management companies?

Quote from @Doug Teasdale: Quote from @Dustin Tucker: Hello Doug,  Here is the Arizona Association of Realtors Forms page.https://www.aaronline.com/manage-risk/sample-forms/residenti...You will probably need to use the Residential Resale Contract.For the Buyer as an example use "Doug Teasdale and/or assigns"  This allows you to assign the contract to your wholesale buyer.