If the obstruction is outside of an "airport area", then generally you don't have to notify the FAA or light it if it is below 199'. The FAA will generally exempt from lighting any structure that is in close proximity to taller nearby structures. So, if you're building a 200' tower within a couple of hundred feet of a 300' building, generally the FAA will exempt the tower from lighting requirements. Case by case.
If the structure is within the "airport area", as defined by a specified slope from the nearest runway, then the 200' limit does not apply and the FAA must be notified of the construction that exceeds the slope limits.
It's been a while since I did those kinds of filings, so I'm working from memory. I may not be 100% correct. I used to do it for radio tower proposals....
IIRC, the FAA determination is not binding on the proponant - IOW, if somebody ignores the FAA's determination of hazard/no hazard, the FAA will have to change the approach limits or MEA of the affected navigation system/airway/approach. There is a way for the FAA to challenge it eventually, but that rarely happens unless somebody pursues it at a zoning commission or other legal body (note that if the construction is a tower regulated by the FCC, in which case the agency will NOT authorize construction without FAA approval). IIRC, the USA Today building in Rosslyn, VA originally had an FAA determination of potential hazard to navigation.
However, once the structure is lighted, those specifications become mandatory.