I would hesitate to say teach yourself to fly a tail wheel aircraft but I guess you could.
Some are more docile than others but they can all bite if you use poor technique.
My 2c (take it or leave it - I regularly instruct on tail wheels so this comes from my experiences converting nose wheel pilots)
Issues:
1. starting -
normally into wind and with stick back to prevent nose overs
2. taxiing -
the aircraft is directionally unstable and can get out of line quickly and will only get more out of line unless appropriately corrected.
the aircraft's wings are at a higher angle of attack and in winds can make life fun
You need to be on the ball when taxiing
you need to keep weight on the tail wheel for directional authority - that at times can mean stick out of wind depending on wind direction
the aircraft will have a strong tendency to turn into wind making taxiing challenging when faced with crossing winds.
watch harsh braking in case tail lifts
3. Take off -
the aircraft is directionally unstable. If it gets out of line it will progressively get worse until it gets nasty unless appropriately corrected.
the aircraft tends to have more swing than nose wheels because during the takeoff roll you will have to push forward to a take off attitude at a speed when you have lower rudder authority.
you need to keep the stick back early in the roll to get directional authority via the tail wheel or skid and then relax the stick as speed builds then actively forward to get a take off attitude as you get more authority
any 'pumping' of the elevator to fine tune or correct the take off attitude will cause swings in different directions.
in a cross wind the weather cock tendency can also add interest to your life
4. landing
- you need to decide what sort of landing you are going to be doing - wheeler or 3 point. Different aircraft may favour one over the other and different conditions favour one over the other. Both use a different landing technique and rely on accurate judgement of nose attitude.
- once on the ground the aircraft is directionally unstable and if it gets out of line it will get worse unless appropriately corrected.
- people unused to tail wheel aircraft have the tendency to relax on the stick or column after touchdown and the tail will lift and this will usually result in a swing. Commonly they will correct for this by pulling back resulting in a swing the other way. The aircraft starts to gyrate left and right as they pump the elevator back and forth. What happens next is a toss up between the amount of directional control they can maintain with the rudder against decreasing rudder authority as the speed decreases. Sometimes they win and remain on the runway. Sometimes they don't.
- depends on type but many don't have good forward vis so you need to be able to use your peripheral vision to judge aircraft height and path through the flare.
- you need to be able to accurately pick the 3 point attitude and if doing wheelers, an appropriate landing attitude.
5. Flying -
this bit does depend on type but most tailwheel aircraft have a powerful rudder (to assist with directional control at low speeds). This means that whilst you still use rudder to counter adverse yaw in flight the amount and feel is different. Typically you will need it or the plane flies out of balance but you need more finesse (rather than 'boots') or it flies out of balance the other way
That may all sound very complicated - it isn't and can be easily picked up as second nature if you get someone to show you and monitor you.
You could teach yourself to do it by reading and looking at the internet. I think however that is not the wisest path or the most efficient.
I reckon it would be way smarter to get someone to show you the attitudes, show you the techniques and allow you to develop the feel for the procedure. A few hours of dual instruction would be safer and teach you way more than you will get by teaching yourself.