Three story 6 bedrooms, 14 radiators 18 Kw boiler oil fired and no problems. It may need an extra expansion vessel if the amount of circulated water increases, if not fed from header tank, as to how heat retained in radiators will affect how heating will depend on control, with oil the boiler is simply switched off/on so if the thermostat is in the room with the cast iron radiators it could increase the hysteresis in the other rooms. With a modulating boiler then it should not really affect the hysteresis as long as any thermostat modulates boiler and does not simply switch off/on.
My sons first house he claimed the boiler was too small and it took ages to heat house from cold, on investigation it was found the lock shield valves had been left wide open, so instead of heating all rooms together, it heated one room until TRV worked and then the next until that TRV worked and boiler was running on minimum output because return water was too hot.
With a modulating boiler there is more of a problem being too big to too small, a boiler may give 6 kW to 24 kW or 10 kW to 30 kW and it is the minimum being 6 kW or 10 kW which has more effect that the max output, as with 10 kW boiler will cycle more so more of a hysteresis that the 6 kW.
I note location of my thermostat means my 18 kW boiler does over shoot the mark by around 1°C even with a Nest thermostat, it is between 4 radiators, hall, shower room, kitchen and living room and what doors are open or closed makes a huge difference to the hysteresis so Nest can't work out how much the over shoot will be as is varies.