For if it's on market seller can just wait for primary residencers to chip in on the deal?

If all the partners chip in, that should be a reasonable cost to insure long-term happiness in the partnership.  

Get more education and keep stacking your chips for now!

As Will said, in most areas, as long as the siding is stable (not chipping, crumbling, or the like) then usually the siding will not have to be replaced.

I took my class with Chip Brown, http://www.realestateschoolofsc.com/I would love to help you more with studying, resources to study, talking about finding properties or anything else of value to you.

Donald, The reasons we are looking at a duplex specifically is one tenant is less headache for us as this will be our first investment property, the lenders we are pre-approved with are only interested in a duplex nothing larger for first time buyers programs, and our city is loaded with side by side duplexes.Just convincing my wife to buy an investment property took a lot of Chip and Joanna Gaines books, and the agreement that it would be "cute" as some of the duplexes are brick Tudors with wood floors, fireplaces, and in up and coming older neighborhoods. 

Broken windows in the basement, downspouts broken, chipping paint.

I've been a builder in Houston for 20 years - I didn't just watch a few episodes of Chip & JoJo and decide I could make a living at this.

I didn't sleep for days and had a chip on my shoulder until I had enough five stars to offset it.

Another cheap option I've done for meetings is ordering some $5 footlongs from subway, a few bags of chips, etc.