New 200 amp breaker panel and new electrical service (all permitted).

I would also look into how challenging certain city codes are with short term rentals, permitting, etc.

Something like: when the foundation is finished, the framing, electric and plumbing are in, roofing and siding, etc   They will usually hold back 20% or so until the house actually has cleared all permits including the final permit of occupancy.  

New permitted breaker panel.

I am looking for a private lender to finance my rehab on an already owned, gutted property in a desirable neighborhood of the city (Upper Lawrenceville): demo complete, structural engineer sign-off, architect-approved design to move the stairs (which is not a small deal in Pittsburgh), and city permit.

I'd appreciate recommendations on reputable hard money lenders, especially those familiar with assisting newcomers.

Also discuss with the contractor the time expected for the project if its small, mid or large and if it needs permits and how long would it take for permitting and all, also payment terms, make sure you go with payment terms that are fair to you and the contractor (so many terms but most common is monthly based on completed work with an upfront for materials) and ALWAYS keep the last payment until project is closed (retainage) and you do your walkthrough and if there's any issues you write them down and provide the contractor with (punch list to release the retainer once they're corrected or fixed). read about how to deal with contractors and always ask for references but it really depends on how big the job is, personally I wouldn't spend too much time doing due diligence on small jobs such as door latches or shelving rather on additions, layout change and other scopes.Good luck!

Get permits up front.

I have gotten a permit for an STR in the county before and was pretty easy. 

Some cities require the STR permit number in the title or very top of the OTA listing so city permit  technicians can scan and keep track otherwise the owner will be contacted and fined for forgetting or shut down if operating illegally.Some cities have a 24/7 STR hotline dedicated to receiving any complaints (from neighbors, HOA) for a code compliance officer to act onSome cities issue expensive fines for those operating without the STR permit