My wife and I own a multi unit building in Chicago and are in need of building maintenance for the roof and siding.The main issue is our building is close to the neighbor’s house.

And a 15 vs 30 should be one aspect of that strategy. 15 v 30 should not define your strategy or goal.

me personally I don't feel to much of a difference on building structure 1 roof x amount of walls just seems bigger space obviously 2 tenants on a duplex = more calls and issues via them as well as double the appliances to maintain  but also double the rent just wanted to pick a few brains and see what people that have walked the walk so to speak feel about it:) thanks in advance

Now local law trumps this and some townships don't require it.Some townships don't require a re roof permit, drywall permit, or painting permit, but every single one requires a building permit for adding finished sqft. 

Also we need a new roof($7k), planning on doing that very soon.

the roof needs a complete overhaul due to sagging, sinking, and the shingles have no more asphalt on them to protect against the weather. 

@Anthony Kondorif you can pull it off write a book on it.The only way we got an out of state bank to back off was to take pics of the roof leaks etc etc.

I know someone who owns a condo in a community were the HOA does NOT cover the roof.  

As for the cost of dues in an HOA, those are typically determined by the age of the property, the level of maintenance required and whether the HOA is putting away enough in reserves as they are required to do so for capital expenditures like new roofs, road work on private roads, maintaining driveways, etc..

Having the roof done, so I have a dumpster on site.  7,200 for the roof500 Dumpster600 Trash out