I've been lurking here for a while. My reloadimg experience was first making and loading leads for my 44 when I was in College in the early 80s. Probably lucky I didn't blow myself up. 

I shoot quit a bit....far more than I want to load for.  However, I'm to the point where I want to put together my hunting loads. I'm probably looking at doing 50-100 rounds a year across each of maybe 5 different calibers, with main being for my Grendel which doesn't have good factory loads for what I want.  I'll just do rifle.

I looked of the sticky that was last updated in 2012.  I know it's like anything....do you want a Ford or a Chevy; F350 or Corvette...etc.

I'm going crazy trying to figure it out.  I know it's a stretch, but I'd really appreciate if someone can point me in th right direction of 'buy this package, plus this' to get me started.  Also, if you are looking to upgrade and got something that you can crate up to me that would just plain work...my IM box has room.....

Thanks in advance. 

you'll soon find that once  you have the equipment to do reloading you'll do a lot more than 50-100 rds per year

My starter list would be:

1. single stage press, my choice would be a Rock Chucker
2. Hornady rifle dies
3. a powered case trimmer, maybe the Giraud Tri-way
4. RCBS military crimp remover and primer pocket uniformers with drill bit adapters
5. electronic scale and backup beam scale
6. Uniflow powder measure
7. loading blocks
8. Dillon case gages first choice, Wilson if Dillon doesn't make 'em for your specific caliber
9. vibrating tumbler
10. Dial calipers
11. hand priming tool of some sort
12. Dillon spray lube or equivalent
13. Shell holders

Then next phase would be go progressive while keeping the single stage press

1. Dillon 550
2. toolhead conversions, etc
3. Dillon pistol dies (technically you don't need Dillon pistol dies for a Dillon press but I prefer them over non Dillon dies, easy to clean, etc)

At this point you could sell off and use the $ to recoup the cost of the Dillon 550:

1. any non Dillon pistol dies at this point)
2. the hand priming tool
3. the Uniflow powder measure

Now you can have the Dillon 550B set up while using the single stage press to size brass for the other calibers

I can't substantially add to AssaultRifler's list, except to suggest some specifics: the RCBS Universal Hand Primer (the one that takes standard shell holders) is an excellent choice for hand priming.  I have that and the Hornady hand tool, and while both are somewhat klunky to set up at first, I think the RCBS tool has better ergonomics.  It also has a more "robust" safety system - which is one reason it's klunky to set up.

You CANNOT go wrong with a Rock Chucker press.  It's solid, sturdy, and stronger than you are.  Mine, made in 1979, has withstood my attempts to do impossible things (it is impossible to push a .40 S&W case through a Lee FCD with the crimping insert in place...) with only some dirt and scuffs to show for it.

The RCBS crimp remover and Hornady crimp remover are excellent tools.  Both are designed to keep Bubba from forking up a primer pocket without really working at it.  Which means anyone with enough brain to type should be able to use them to remove primer crimps, leaving consistent and SAFE pockets.

A traditional, balance-type powder scale is a must.  Even if you have a high quality digital scale, a balance will be the way you verify the digital scale is accurate.  That's science, not just "we've always done it this way."

Thanks guys.  I can work off this list.  As for budget, I'm goimg to spend as little as possible. EE here I come.

The Rock Chucker is a good press, no doubt, but it can be slow as can any single stage.

Consider a Lee Classic Turret, with the cast iron base and four hole turret.  Despite adding a progressive to my bench, my turret still gets used for my low volume calibers like 44mag and 38spl.  Without racing, you can get up to 150 rounds per hour with the turret for pistol calibers with carbide dies.

The OP wants to make 50-100 rounds per YEAR.

This is a modification of the list offered by AssaultRifler.  I think it is a better example of a "starter kit".  

For every item, look for used equipment.  In general, used reloading gear works as well as new and costs less.

1. Press (consider the LEE classic or other less expensive press)
2. Dies (LEE dies work and cost less)
3. Case trimmer (anything inexpensive)
4. <deleted>  
5. Beam scale
6. <deleted>
7. Loading blocks
8. Dillon case gages
9.  Powder Pal (funnel and measuring pan in one item)
10. Dial caliper
11. Hand priming tool (RCBS, only if the press does not have one built-in)
12. Imperial Sizing Die Wax
13. Shell holder(s)

A measuring spoon from the kitchen works very well to dispense powder into pan.

Clean cases by hand using a towel.

Use commercial brass (no decrimp needed).

Add Hornady headspace comparator with bushing set to the list.

Yep, there are lots of nice tools out there which facilitate reloading.  

For low volume, starter kit, you can just use the rifle (chamber and bolt) in lieu of a case gage or comparator.  

Also, you can just resize to the die's machined-in headspace with no special gaging needed.  The brass won't last as long but at 50-100 rounds per year, does it really matter?

I started with the Lee Breech Lock Challanger set that Midway carries, it's only $130 and includes almost everything for a basic setup. I was reloading 1500+ rounds a year with it before I "upgraded". For 50-100 a year it's plenty of press. You'll need dies and a way to trim cases, there's a "what else do I need" list in the description. Add some harbor freight calipers and your set for somewhere around $200.