Yes, of course I would get rid of that jerry rig. 

But, this type of situation may create more opportunity for an investor, since it is not as cookie cutter as many investors would like and they may not be able to recognize the nuances or opportunity with some deals.

As others have pointed out, flips are not eligible for 1031 exchanges.You are not required to keep buying up when you do flips.Flippers normally look for cookie cutter projects to work on so things can be more predictable.I.E. they may look to buy 3 Bed 1 Bath for $50,000, put $40,000 into it and look to sell it for whatever the ARV is

He then had the slab of gypsum shipped by rail to Chicago where he had hired a stone cutter named Edward Burghardt to carve a giant.

Or worse yet, when I see a cookie-cutter lease used requiring 30 days notice vs the 5 days permitted by law and granting all sorts of other rights to tenants that aren't required by law. 

Like you said there are some wonderful neighborhoods, especially where they call it the "West End" near Assumption and Worcester State, some beautiful side streets, lots and houses...not your typical cookie cutter style houses, lots of tudors and homes with great character.

I sold my last house in Isanti last fall for $175k (4BR/2BA cookie cutter house). 

PS would love to chat with you sometime, I think you know my buddy Justin Cutter. 

I had an appraisal on my personal residence two years ago and it was way off...and I live in a national builder neighborhood where all homes sell within a very tight price per sqft (cookie cutter). 

A lot of PM contracts and agreements are cookie cutter.