Do an assessment on major stuff (roofs, paving, siding, windows, HVAC/HW) and figure what's less than 5 years. 

Dear Victoria,I do not share your optimism and do not believe that your assessment of the stock market is entirely relevant to the benefits of investing in Philadelphia real estate.While you’ve gone out of your way to provide a number of compelling data points on the market, I think the balance sheets of most public traded companies tell a very different tale.

Hi @Kristen G.I agree with Aaron's assessment that the majority of the value would come from the increase in square footage and not necessarily the addition of a 5th bedroom.

Just remember that for property taxes typically a new assessment will happen every four years (at least in Ontario) so if it says last assessment was 2016 then you’re probably up for a reassessment soon after you get the property.  

Get an actuarial assessment of the pension fund's health from a neutral 3rd party. 

That's probably because people are using the bank's money, not their own money, and do not assess risk properly.

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Are there any certain websites or anything that help you find this assessment on a neighborhood?

Through this special assessment, I would have to front about $7,800 dollars.

Knowing that will allow you to review the subject property to assess its condition in the market and what updates are appropriate for re-sale.Before you even start down that road, perhaps you ought to do a trial run or two, or at least perhaps consider finding a mentor to shadow.