Real old pilot here. Learned when there was no requirement for a tail wheel endorsement.
I have over 3000 hrs in C-180’s.
I have about 5000 hrs total in tail draggers of all types and sizes.
I gots lots of stories but that is for another time.
Wise old pelicans told me and I always remember and never forget:
The only time to relax when acting as the pilot of an Beech-18 ( twin engine tail dragger ) is after it is chained to the ground and you are 100 feet away.
Mass, mass, mass… ( C-170 and C-180 are not much different in size and the power difference at idle upon landing is minor but the mass… A lot of C-170 drivers have a real hard time in the much heavier C-180… You got to remember the mass…
Stance has a lot to do with it also. Piper Cub has narrow main gear and the t/w is far back in comparison. A Swift has a wide main gear with a short distance to the t/w. Plus has less rudder authority at landing than a Cub. Guess which one will spin like a top at the least bit of inattention?
As to the actual reason so many early planes were made ‘conventional’ was due to the fact there were far more unimproved places to fly from / to than clean paved airports. Strength and ease of construction, Plus propeller clearance were most of it. It was so important that many of the inline engines were set up as inverted engines ( Messy and with many problems) so as to get the most clearance for the propeller as in some models of the Fairchild-24, the BT-26 and other planes designed in the 30’s. Also the engines were mostly radials which meant the blades need to be longer for comparable HP engines because of the width of the engines were so big, and many aircraft used wooden propellers. Even metal props were slow to go to three or more blades due to the start of the art and the materials available at the time. ( there are always exceptions, 4 blade wood was seen on some of the early,big, multi-engined a/c of the day )
Not all t/w aircraft are hard to land. The little Stinson-10A ( 2 place, 65 HP, fabric ) was such that when it was time to land, the procedure was to close your eyes and pull the throttle to idle. That little plane would go find an airport and land by itself. A total delight to fly & it would make even a dead pilot look like a master of the Taildraggers…
Many WWII large aircraft were made with a t/w due to conditions they had to operate in.
In small single engine aircraft I prefer a t/w aircraft in really nasty cross wind conditions when I really have to land at THIS airport because that is my only choice due to fuel or weather, etc… I can land diagonally and run off into the grass or even land on the grass, cross the only runway at an angle and into the grass on the other side without damage to the aircraft and a tricycle geared a/c would be much more likely to be damaged.