Welcome to the forum and thanks for asking our advice
For small amount of ammunition, the investment in the Lee Loader might be best. At least the price of entry is low (about $25-$30, right?).
Add a mallet (Do not use a steel hammer. Steel on steel is not advisable.) A wooden, rawhide, plastic or very hard rubber is much better. Even a brass hammer, but not steel.
A chunk of wood underneath the tool helps reduce damage to your work surface and can be replaced with another scrap when it gets all dented.
Use a drop cloth spread out under your chair and work surface. It will make cleanup simpler and will catch the (inevitable) powder spills, dropped primer (either live or used) and the gritty, burnt trash from the spent primers. Don't use plastic sheeting. It is noisy, lets primers roll away and the static it collects causes spilled powder to scatter. Cloth drapes better, too, laying flat and not tangling up your feet.
The Lee Loader comes with a single powder measuring dipper, but that severely limits your capacity to choose different powders or power levels. The entire set of dippers costs about $15-$18 and will allow you more flexibility.
Even having the set of dippers, however, does not make it easy to get the charge you want for adjusting the power level of your ammunition. Most loading data comes in weight, not volume, so you have to use the Lee conversion chart to figure out what you are getting. Even so, if you desire a charge weight in-between what the dippers give you may be tricky, so a scale is a good idea.
A scale to actually weigh the powder directly is far more flexible. $25-$30 will get you a Lee Safety Scale. It is accurate to .1 grain. (Note: Gunpowder is measured in grains, which is a unit of weight. 7,000 grains make a pound. Do not confuse grains with granules/grains of powder.)
The Lee scale, while accurate, is not easy to read. (Put it up on a stable shelf at eye level in good light is my advice.) Ohaus makes scales that, while no more accurate, are easier to operate. Ohaus makes almost all the scales sold under the nameplates of RCBS, Dillon, etc. Those scales cost from $75 to $180. I don't recommend electronic scales. Many do, but I don't. Gravity is reliable. Electronics can be affected by the electronic emanations of flourescent lights and by low battery power.
Having a scale will allow you to customize your loads (with the information contained in loading manuals or from powder manufacturer's web sites) with infinite variety.
So:
A Lee Loader can fit in a jacket pocket, but you have to add the mallet, a work surface, eye protection and ear protection (the repeated banging of the mallet is not good for your ears) you wind up with a shoe-box full of gear.
If, however, you take out the wood worksurface and put in a scale, take out the Lee Loader and put in a set of press-mount dies, take out the mallet and put in a Lee Hand Press, you can load much more flexibly and quieter.
$30 Lee Loader
$10 Mallet
$0 Scrap wood worksurface
$0 Eye protection and ear protection, which you already have for your shooting (DON'T YOU?!?)
$10 protective glove for your off-hand (just in case a primer goes off)
$35 Lee Dies
$30 Lee Hand Press
$0 Eye protection and ear protection, which you already have for your shooting (DON'T YOU?!?)
$7 loading block (not necessary, but recommended, $0 if you make it yourself)
To either choice, I would add the $25 Lee Safety Scale (or a better one if you choose), the $15 set of Dippers and a couple of loading manuals (Lee's book and Lyman's, perhaps)
The price difference is not that much once you consider all the accessories you will eventually find you want.
The hand press is your ticket for both simplicity and portability.
Starting slow and learning every step is the smart thing.
While I don't want to second guess your decision about the Lee Loader but I will anyway because I think a press will serve you better. Though either will let you learn the steps, the press lets you see very closely how it is loaded and with conditions even more controlled than with the Lee Loader.
The mallet driven tool requires you have a sturdy work surface and be away from other people who will be annoyed by the hammering. The hand press can be operated quietly seated in front of a card table. (Though, the scale I recommend needs to be on a more stable surface.)
The Lee Loader is perfectly adequate and probably as fast as the Hand Press. And is an investment commensurate with 20-40 rounds . For about $25 more, you can have a much quieter tool that is not unnerving to onlookers waiting for the explosion (said explosion is virtually impossible, but EVERYONE thinks about it - probably from watching old cartoons).
Check out these videos
http://www.youtube.com/watch?v=0-LA2G_Sy4I Lee Loader
http://www.youtube.com/watch?v=K6IoNCtFHwUhttp: Lee Hand Press.
The continuum of convenience and speed goes up from there
If your shooting goes up past 50 rounds at a session, you might find yourself thinking a press actually mounted on a tabletop would be convenient. It is. And faster than either the Lee Loader or Hand Press. But the price starts to climb past $100. Maybe up to $200. But that is barely 7-10 boxes of ammunition.
Lee makes a $30 single stage press that is an EXTREMELY basic setup, but the Challenger or Classic Cast single stage will last your lifetime or more.
If you want more speed, a Turret press and some accessories will get you up to 100-200 rounds per hour rather than the 30-50 available with the simpler tools. But the bench-mounted single stage press or the turret is no more complex in operation than the hand press. You are looking at $250 for the setup.
If you still want MORE speed, a progressive press can give you 100 to 1,000 rounds per hour. But they are more complex and will cost you some serious money. $200 to $1,000
Food for thought. If you think the gear is costly, add up a year's worth of retail ammunition purchases and compare.
Lost Sheep
Lost Sheep