From someone who's only been rolling since last summer (July)
WLT kits are great. When I started I assumed that I wouldn't like the cigars made from the kit. The kit was 40 bucks, to to me, that was the price I would pay to learn HOW to roll. Once I learned HOW to roll a decent cigar then I played around with different leaf blends. I've rolled many that were terrible, and then a good many that were terrific. My earlier mistake was hashing some leaf together, let it rest a day, smoke it to fine out it was wonderful but I forgot what the blend was. So, write everything down when making a blend.
Don't worry about making your cigar look like one you can buy. Just make it smokeable.
So you order a kit of leaf. make some cigars and get started. You'll quickly learn what equipment you actually NEED to make the job easier.
Incidentally, you can play with leaf ratio with the leaf kit to see how moving the amounts around affect the flavor and taste of a cigar.
It's actually a lot of fun once you get into it. I now prefer the taste of my own cigars over the taste of commercial cigars.