Some of their installers do not pull permits and such but you can pull your own permits.   

TLDR: $750k house in best part of town on a $140k single person salary, with a $2500 mother-in-law suit and 2 extra airbnb rooms. 

Ian, please message me with the contact information for your property tax appeal specialist.I was told by Scott Phillips at Allegheny County that the increased assessment is due to permits being taken out to do a major rehab on the house by the former owner.However, as an attorney, I know that the county cannot simply send out an increased tax bill without first sending out a notice of an increase of assessment like it did because that violates due process.Thanks.

They will give you insight to their zoning and permitting process.

Spend less than you make and the extra will accumulate.Get a second job.Cut expenses.Sell stuff.Borrow - personal loan, credit cards, HELOC or cash out refi on a property you already own, 401k loanfriends and family

Have you thought about just buying a SFH then renting the extra bedrooms out.

This will all have to permitted by your city, along with permission from the current owner.Have you considered purchasing the entire parcel and renting the main home back to the current owner?

I personally would want a decent cash flow and not be dependent on any future appreciation that may or may not happen.If you want to use a PM then add that into your analysis and make sure it works with this extra cost.I have always been told to add in the cost of PM whether you do it or hire it out.

I like to spend a little extra on those to really make the place pop.

I've  always thought renting to Section 8 tenants would be one of the safest ways to get rent paid on time minus the fact that some may have to pay a little extra out of pocket.