@Tushar Shah I didn't realize that you were from Chicago when I initially read your post; I'm sure you run into a lot of the same issues many investors do here as well. I will say it is a quite unusual that there is one common furnace for 6 units. This exacerbates the problem mentioned before regarding individual unit control, as well as raises an issue of where the return air is ducted from (i.e. if there is a smoker or otherwise unpleasant smell, that will get circulated through all units).
1. I don't have experience with common hot water, so I could only provide a guess. I suggest finding out the capacity in gallons and the heat output measured in BTU's, and do some research to find out if it's sufficient. You could even ask tenants of their experience to get a undoubtedly honest review.
2. There isn't much in the way of maintenance for a hot water heater, other than two things: 1. making sure the thermostat is set at the middle heat setting (usually noted by A, B and C, with C being the hottest). Perpetually leaving a HWH at the highest temperature setting shortens the life span. The other maintenance item would be to drain the tank once a year to remove any sediment that gathers at the bottom. Both of these are things anyone can do without the help of a professional.
3. Yes it would definitely be extremely expensive to retrofit a building that size with new plumbing, even more so here in Chicago because code does not allow PEX, only copper. I would definitely use it as a negotiating tool if found during inspection. Happy to refer a plumber that changed out my old galvanized for copper in one of my buildings, just PM me.
4. The cast iron pipes are a non-issue, those would only be relevant if you had radiant heat boilers, which you already mentioned is not the case.
5. Typical general inspector should be knowledgeable enough to provide insight into the condition of the tuckpointing. In my opinion you don't need to hire a specialist for this. If the inspector says there are some issues it may be worthwhile to have a mason provide you a quote to further leverage your negotiation.