I have to chuckle a bit at naming the "worst" villages to do rehabbing in based on how tough inspectors are. The plain reality is they are doing their job and like it or not, they are tasked with bringing the house into code for the protection of their resident or future resident. I am familiar with the "rudeness" but that unfortunately is not so uncommon when dealing with government employees who have to deal with the public on a daily basis and is something you just have to have thick skin for. As for towns that have a difficult permit process, I think you could literally say all of them especially those that use a third party inspection service to handle their inspections. I say that because you may have different inspectors calling out different items at each inspection for instance you may do a rough electrical inspection with one inspector and do a final with a different inspector that see's things a little differently forcing you to redo work already inspected. It can be frustrating for sure.
Evergreen Park was mentioned above and is a good example of a town that can be difficult but not because the inspectors are a problem. The issue there is the $10,000 cash bond they require when applying for the permit and the length of time it takes to get your money back when you successfully complete work on the property. If you know the ropes there and what the village expects, the actual permit and inspections are generally pretty straight forward.
Towns like Romeoville, Streamwood, Aurora, and Arlington Heights take 3-4 weeks usually just to obtain a permit whereas I have seen towns like Woodridge, Plainfield and Orland Park turn around permits in 10 days. That said, I think the reason many building departments are so stringent with investors is the illusion that most are looking to cut corners for the sake of profit. If you are investing in flips make sure the scope of work you come up with during your inspection period prior to closing is taking into consideration town building codes. Typical "surprises" for investors are ELECTRICAL hard wired, interconnected smoke/carbon detectors - tamper free outlets and 20 amp GFCIs at kitchen counters, romex or bx wiring and covered closet lighting. PLUMBING expansion tanks for hot water heaters, copper scabbed into galvanized pipe and proper venting HVAC - sealed duct work and properly sized for sf. That is just the tip of the iceberg so to speak but usually tripping points for newer investors.
Bottom line....nothing is "grandfathered in" usually, inspectors don't care about holding costs and there are very few cosmetic only rehabs that don't require some sort of inspection. My advice is to have at least a 15% contingency reserve going into a rehab and your numbers should work out better.
May your bottom line always be above the water line!