What's the difference between part 61 and part 141? I've seen memes but never really heard the real story.

From the FAQ:

Q: What’s the difference between 61 and 141?

Part 61 and 141 refer to the regulatory definitions of different schools. Part 141 is often called an FAA-approved school. This doesn’t mean Part 61 training is some wild west cowboy nonsense, it just means that the school itself isn’t FAA supervised and operating on an FAA stamped syllabus. Part 141 has those things and can then offer a reduction in training times. Realistically most people don’t finish in the minimum amount of time anyway.

Part 61: Basically anyone doing training independently or at a “small” school is likely part 61. The training will look much like private tutoring or some kind of coach. You will meet with an instructor on your own schedule and work on whatever you need to work on for you that day. The vast majority of instructors still have a training plan or syllabus they work from and your training can be tailored to what works best for you individually. The legally required minimum number of flight hours to obtain a private pilot license from this type of training is 40 hours. The national average hovers somewhere in the 70s.

Part 141: Often larger than part 61 schools, these operations will have the aforementioned FAA-approved program. This means you can obtain a private pilot license in as few as 35 hours of flying, although that’s somewhat atypical. Training is organized and required to follow a pre-approved syllabus. Some people find this structure helps them learn better, some find it restrictive and stifling. These schools, very broadly speaking, tend to be more expensive. If you finish in fewer hours, this can work out to your advantage. Often these are called pilot mills because many of the most well-known 141s are very big, crank out as many pilots as they can as fast as they can, and aren’t respected for quality or competence. These are also often the largest brand names in the business. Aeroguard, CAE, L3 Harris are all considered pilot mills and are best avoided.

Also, how much harder is takeoff/landing in a tailwheel aircraft as opposed to tricycle?

It depends entirely on the aircraft; different taildraggers have very different handling characteristics. Landing is typically more challenging than taking off since landing with a drift or side load immediately gets a swerve going; takeoff tends to be a bit less dynamic.

A gentle trainer like a Citabria will let you know you need to pay attention but it takes a lot to get in trouble. Something like the Helio Courier I used to fly is a very different matter. Especially on pavement, if you let a swerve begin to develop at all it can quickly become unrecoverable.