We bought a property that we feel is assessed by the our local government too high.

The latest red flag is his belief he purchased a "fully renovated" property in Philadelphia for $115K.

. $40k a year for not doing much is a great investment on $40k unless you are putting in a ton of work into the property.Who operates the property?

Without the upside of a good neighborhood and/or quality property, I don't love it. 

@Anthony KlemmCan’t find a rental property to cashflow?

For a condo you can/should check the county assessor for land value  (you would apply the same allocation %, don't use their actual number listed) Also check your HOA documents.

I do emphasize on showing that my 1800 property is not going to magically become modern. 

@Georgy Cherkassky"Not entirely, if your saving 1 grand a month for a downpayment on property; your first property will be in three years and then you will have to save for another 3 years to buy a second property, so on and so forth."

And they don't have evictions, busted furnaces, or the hassle factor of property. 

Max of three rental properties.