It looks very similar to this style oven.

C deals are the older garden style 60s-70's built buildings that have been maintained, but still have low ceilings, etc.  

My goals: Enough cash flow in multiple properties to- help family out who are struggling - retire early- travel in style!

My goals: Enough cash flow in multiple properties - help family out who are struggling - retire early- travel in style!

I heard Steve Cook discussing his life changing life style on Michael Blanks Podcast. 

In my experience, most folks start looking for bigger deals by the time they reach 10 SFR style properties anyway, so it's typically not a huge deal.

If this is the typical style I would repaint it and paint the brick foundation.If this type of siding is an outlier I would replace it and possibly force more value into your home.I'm a huge fan of the pre-painted fiber cement even though it is more expensive.

If the practice of this style of redevelopment/development is common you'll also have local developers with a playbook.  

Taking a warranty deed and chumping it down to a quitclaim deed?  

I feel it's worth it, based on basically zero vacancy rates and very low turn over (we are typically under 15%).I expect the market for high end multi family to reach a saturation point soon, probably putting pressure on high end rents, but there will always be a subset of tenants who prefer the life style of a single family home in a residential area over an appartment building, even if it's really nice.