It is very much case-by-case and requires understanding of the current regime for personal itemized deductions, as well as gambling on the proposed changes to this regime by the current administration.

Quote from @V.G Jason: Quote from @Jay Hinrichs: The mindset of cash flow is everything and appreciation is just luck or gambling or whatever these folks say is one of the worst mindsets I see on BP.

Simple appreciation is a gamble because you have no control over it, so don't consider it.

A big question is do you have the $25,000 to gamble?

Better materials such as stronger  lumber were used when the earlier vintage properties were built and many  contained design characteristics such as stone or brick work and intricate millwork that are too costly to replicate today meaning many buildings are significantly below todays replacement cost. 

Does the parcel have unique and challenging characteristics?

In a waterfall, the GP is incentivized to stay the course, gambling the LPs equity, because the GP only makes money above 7%. 

Depending on the zip code I was wondering could I gamble with them on a fix and flip or brrr.

I'm ok with gambling on it.

If no issues arise, it's likely the subto has all those underlying positive characteristics you mentioned.