Do you have enough flat surfaces where the wheels will work in the places people travel.
How cheap and dependable can you build it without adding too much weight to the luggage.
Are there enough people traveling and carrying their own luggage for them to purchase this.
Ever lugged a huge wheel-less piece of luggage around a big railway station? I have. It is hell.
Traveling salespeople etc. would often go on relatively short trips, even in the steam engine era. We underestimate mobility of pre-WWII people by a lot...
The point about simpler clothing is really interesting. I can imagine that this could be the crucial difference.
> The first railway hotels in London were built at Euston. Two hotels designed by Hardwick opened in 1839 on either side of the Arch; the Victoria on the west had basic facilities while the Euston on the east was designed for first-class passengers
And in Manchester:
> The Grand Junction Railway, Britain's first trunk line, was completed between Curzon Street railway station in Birmingham and Warrington Bank Quay railway station, Warrington, on 4 July 1837. Through trains began to convey passengers from the station to Birmingham, and a separate booking office and waiting room were provided. From 17 September 1838 there were through carriages to London Euston by some trains after completion of the London and Birmingham Railway in that year. This increase in long-distance services resulted in one of the first private railway hotels opening in Liverpool Road.
Here it is: https://manchesterhistory.net/manchester/tours/tour1/area1pa...
https://en.wikipedia.org/wiki/Euston_railway_station#Old_sta...
https://en.wikipedia.org/wiki/Manchester_Liverpool_Road_rail...
Although perhaps I misunderstand your point--if your point is about someone else carrying the bags, maybe. But if that's the case, then why restrict it to flying, as opposed to travel by train or car?