Don't get me wrong; there are plenty of issues/problems/quirks that old houses have that new houses don't, and an old house can obviously have hidden problems and big repair/maintenance bills too...but, the point is: a brand new house is not a foolproof solution to repairs/maintenance (and in some cases, a brand new house can be a much bigger gamble than an older house).This is a particularly important lesson for inexperienced investors, who tend to be the most prone to "shiny object syndrome" (the tendency to let nice aesthetics distract from real, underlying issues).

When contemplating such a move one might want to evoke the immortal words of Clint Eastwood's question "do you feel lucky punk... well do ya?".

Has some difficult to replicate design, features, or aesthetic?

Perhaps keep it to more aesthetic type improvements, updating, etc. 

But also lets you look at less tangible factors such as location, potential appreciation, aesthetics in a way that is separate from the changing dollar value.I recently had an opportunity to buy a property for $250k, but it was difficult to value One thing I realized was that I would have happily traded 2 (easier to value) properties I owned worth $150k apiece for the new one.

My biz partner also considering it for aesthetics and resale.  

My instinct is to tell me dad no and just buy the cheapest aesthetically good looking fridge I can.

I'd redevelop the property into 2-3 bedroom units with an 'island-modern' aesthetic. 

Do I included aesthetic decorative things like accents walls?

My limited qualification is that I analyze, buy, and sell several beat-up houses and land each month.Objective, non-opinionated summary: Councilman Darrell Clarke and the Strawberry Mansion Community Development Corporation have pushed a zoning overlay that prevents higher unit density on land, building heights, roof decks, and other development characteristics non-homogenous to the current neighborhood aesthetic.