The 38 spl is probably one of the easiest cartridges to learn on - I don't know what you are doing for projectiles but wander on over to this site
Cast Boolits
It's easy to join and you can usually pick up lead projectiles at a reasonable price from some of the suppliers. There's nothing wrong with a Lee Classic - a lot of folks have been using 'em for a lot of years. Get a good manual and read the pistol cartridge loading section. You will find data for the 38 spl that will give you the load for certain projectiles, etc. It will give you the minimum and maximum grain wt. for the powder. A lot of folks utilize dippers and they work fine. Just start low and work your load up. Once you determine your powder that you are going to use - there are a number of good ones for 38 spl - you can always make yourself a dipper out of a cartridge case cut down to the correct size for you load. I believe the Classic comes with a dipper and a chart?
If you decide once you start reloading to make a step up in your equipment - before buying new, check out eBay and the like. I bought a RCBS single stage Junior 2 and a Junior 3 very reasonably and they, like others, will do everything thing you need to do.
Google Titan - they handle Lee and are very competitive on their prices. It's not necessary to tumble your brass - shoot it and reload it. If you want it pretty, then as mentioned, you can wash it and clean it up. The link I gave you has many different threads on lead bullets, equipment, casting, loads, etc. - it's a great sight and you can learn a lot over there - don't be afraid to ask questions.
Be safe, do your reading and research and don't push the limits on the loads you do. Get on different reloading forums as there is a lot of good information out there - just sort it out and if not sure, ask. Good luck, be safe and have fun. I cast my own bullets and have the brass so the only expense I really have is the cost of the primer, powder and my time which I have plenty of - beats the price of the ammo on the shelf.
By the way . . . if you don't have or haven't saved your brass, you can usually buy used brass from a number of sources - I recently purchased a 1,000 plus once fired brass for about $70 - usually you can get it for between 6 and 8 cents a casing for 38 spl.