Welcome to handloading and thanks for asking our advice.
My prejudice is to assemble your own kit. Look at the contents list of a number of kits (write them down) and decide what pieces of equipment you will actually use. For example, if you load straight-walled cases and use carbide dies, you will not need case lube or a lube pad. If you load for revolver, you may not need a caliper. I didn't for decades. You will PROBABLY need a bullet puller someday, but few kits include one. But the, I did not have one for several years, and even after I got one, it was another several years before I actually USED it.
The fact is, it is possible to load with only three things. P.D.S.
Press, because hands are not strong enough to form metal
Dies, because fingers are not accurate enough to form metal
Scale (or Scoops), to measure powder, because eyes are not accurate enough.
It would be crazy to load without some other things, Manuals, eye protection, stuff like that. But the fact is, physically, you can load very simply, albeit, slowly.
You can get older manuals and the excellent "ABC's or Reloading" from your local library. Almost all manuals have their early chapters devoted to a description of the loading process and it doesn't matter how old they are (as long as they don't pre-date smokeless powder). A drop cloth can be had from an old sheet. Other pieces of equipment can be bought as you find need for them (if you live close enough to a retail outlet).
All the other stuff just adds more safety, speed, accuracy or convenience. All good things (which you have the budget for), but which can wait a little while until you get your feet wet and have determined your personal loading style and preferences.
A good-quality (last a lifetime quality) single stage press can be had for $80 and up.
A good set of Tungsten-Carbide or Titanium Nitride dies can be had for $30 to $50
A set of Lee Scoops can be had for $15, or a perfectly accurate scale for $25 to $100
A 2x6 and some carriage bolts to mount the press may be already in your garage, along with a "C" clamp you can use to clamp it to a coffee table (properly padded with cardboard, towel or newspaper). I used to wedge mine in the drawer of an end table, no "C" clamp at all.
With your budget, you can afford to buy a good kit adequate for your needs and be loading by the weekend. But if you put the thought required into assembling your own kit, you will be loading a tiny bit later and slower at first, but the learning curve will be steeper and faster, in direct response to the greater effort involved. But worth it.
The one kit I would recommend as a core is the kit offered by Kempf's Gun Shop with is built around the Lee Classic Turret (superior to Lee's Deluxe Turret), Deluxe dies (most kits do not include dies), a primer dispenser (you could use your fingers, but this is well worth the cost) and a powder measure (you could use scoops or a scale alone, but a measure is SO much more convenient). The only thing lacking is a scale. (Lee makes a scale for about $25 which is as accurate as any of the others, but some find it difficult to read and it only goes up to 100 grains, plenty for powder, but measuring heavier bullets is out of its scope) Since Kempf's doesn't make you take a Lee Scale, you can add a Lee, Ohaus, RCBS, Redding or whatever is your preference. The only real nonessentials in Kempf's kit is the ammo boxes they include.
Add powder, primers, brass (once fired from retail-bought ammunition is the way I go) and bullets and you are loading
Let me share with you some posts and threads I think you will enjoy. So get a large mug of coffee, tea, hot chocolate, whatever you keep on hand when you read and think and read through these.
The "sticky" thread at the top of TheFiringLine's reloading forum is good, entitled, "For the New Reloader: Equipment Basics -- READ THIS FIRST "
thefiringline.com/forums/showthread.php?t=230171
The "sticky" thread at the top of TheHighRoad.com's reloading forum is good, entitled, "For the New Reloader: Thinking about Reloading; Equipment Basics -- READ THIS FIRST"
thehighroad.org//showthread.php?t=238214
The first draft of my "10 Advices..." is on page 2 of this thread, about halfway down.
rugerforum.com/phpBB/viewtopic.php?t=13543
outdoorsdirectory.com/showthread.php?t=43055
rugerforum.com/phpBB/viewtopic.php?t=22344
"Budget Beginning bench you will never outgrow for the novice handloader" was informed by my recent (July 2010) repopulation of my loading bench. It is what I would have done 35 years ago if I had known then what I know now.
rugerforum.net/reloading/29385-budget-beginning-bench-you-will-never-outgrow-novice-handloader.html
I have a thread "To Kit or Not to Kit?" that describes different philosophies of buying or assembling a kit one piece at a time.
rugerforum.net/reloading/33660-kit-not-kit.html
rugerforum.com/phpBB/viewtopic.php?t=13543
Minimalist minimal (the seventh post down)
rugerforum.com/phpBB/viewtopic.php?t=107332
Thread entitled "Newby needs help."
thefiringline.com/forums/showthread.php?t=430391
My post 11 is entitled "Here's my reloading setup, which I think you might want to model" November 21, 2010)
My post 13 is another version of my "10 Advices for the novice handloader" November 21, 2010)
Thefiringline.com/forums/showthread.php?t=439810
thefiringline.com/forums/showthread.php?t=448410
Good luck.
Lost Sheep