Here's my advice... (caveat, I'm very concerned with my own safety and the safety of those around me)
1. READ. Get the ABC's of Reloading, the Speer Manual and the Hornady Manual. Read the details on how to reload cover to cover in all three, and especially pay attention to the section on checking for over pressure. That will save you a lot of headaches and potential danger. I cannot emphasis this point strongly enough. The information contained in these manuals will save your life. Plus, you will have manuals with a ton of reloading data that you can cross reference when working up loads.
2. Start with a Single Stage or Turret Press Kit. That will give you the ability to learn the ropes safely and you will never outgrow this machine. I started with an RCBS Rockchucker Supreme Kit and still use the press and all the included tools to this day. The Kit gives you almost everything you will need. I mainly load Rifle calibers on my single stage and use it to deprime brass these days. If I were to do it all over, I would probably have bought the Turret Press in a Kit. A Redding or Lyman Turret would be the way to go. Some have started with a Progressive, but believe me, for a newbie, that is a problem waiting to happen. Reading about something and doing it are two very different things and a progressive press has a lot going on that you don't need to be distracted with when learning. The Turret Press will also allow you to safely increase the volume you reload.
3. If you go with a Single Stage Press, convert it to use the Hornady Lock n Load Bushings or the Lee equivalent. That will make life a lot easier. Since you can set your dies once and easily install and remove them without having to re-set the dies.
4. Lee Dies are fine to start with. They load excellent ammunition, are easy to adjust and are very price competitive. The 4 Die Carbide Pistol Set will eliminate the need to lube your pistol brass and you get the Lee Factory Crimp Die. This way you can seat and crimp in separate operations and the carbide sizing ring on this die will iron out any issues with your case before you shoot it. The Lee Dies also come with a shell holder and powder dipper. Other manufacturers charge for this.
5. Stick with a traditional beam type scale to start, like the RCBS 5-0-5. They are a lot less finicky than the electronic scales. These scales will be included if you buy a press kit. You can buy a set of check weights to ensure your scale is accurate. I've found mine very accurate and repeatable.
6. Use a powder baffle in your powder measure. The Powder measure is generally included in a press kit. The baffle may or may not be included. The baffle will help make your charges more consistent. It's a piece of bent metal that sits in the measure and holds the powder above it, while allowing powder to trickle down to the hopper while preventing stacking.
7. Invest in an LE Wilson Cartridge Gage for each caliber you load for. This will ensure your brass and loaded rounds are in spec. I like LE Wilson, since they cater to the high precision crowd and their tools are very accurate.
8. Get a Collet Bullet Puller Die, like those made by RCBS or Hornady. You will need to purchase a caliber specific collet for each caliber you load for, but this will make disassembling rounds easy and safe. Don't waste money or time with an inertial bullet puller.
9. Get a notebook and accurately record your load information. That notebook will really come in handy. Capture your caliber, case make, powder charge, primer make and bullet make, weight and type. Also, date you reloaded the rounds.
10. Invest in a good set of dial calipers.
11. Wear Eye Protection
12. One other tip that will help...Invest in a Lee Universal Decapping Die and a Frankfurt Arsenal Wet Tumbler for cleaning your brass. Decap the fired dirty brass with the Universal Decapping Die, then throw it in the wet tumbler and let that machine clean your brass (AND primer pockets) to like new condition. These two items have been game changing for me!
Starting with a friend who is experienced is a good way to go, but remember... READ FIRST, so that you can ensure the information your friend tells you is accurate.
Let us know how you make out and if you have any questions, post them or PM me...