wow, even if i had to start all over i'd be hard pressed to spend 1k on relaoding hardware, but it's a problem i wouldn't mind having.
i think most people will tell you to start off with a single stage press, to get a better understanding of the reloading process. you'll probably want to have one anyway for small batches, load development, and other odd jobs. so if i were you i'd start off with one. they can be had really cheap used.
next, or first if you like, get a reloading manual and read it. brand of manual is nothing more than personal prefrence, every one i've seen will give you the ins and outs of reloading, what to do, and more importantly what not to do.
then get some dies. again brand is a matter of prefrence, some are better than others, but all will get the job done. for pistol calibers, i would get carbide dies. not necessary but speeds up the process as you don't have to lube cases.
powder measures of some type are obviously absolutly necessary. you can get anything from lee dippers (nothing more than calibrated spoons) for $10 to the most expensive auto dispensing scale. i started out with the dippers and went quickly to a balance type scale.
powder dispensers are not necessary, as you can weigh charges individually, but do save time. i don't use one cause i tell myself it's more accurate to weigh each charge (which it probably is), but in reality it's cause i'm a cheap bastard.
you will also need case prep tools, i.e. trimmer and such. there are case trimming stations, which i have no experiance with. i use lee trimmers, which are simple to use and impossible to f-up. you will also need to chamfer and deburr the cases after trimming. there are special tools for this, but i use a old reaming bit i "borrowed" from work and sandpaper. some people will tell you you need a primer pocket cleaner. it's a tool that costs about $5. i've been reloading for 5 calibers, rifle and pistol for about 5 years now and have never once wished i had a primer pocket cleaner or even had the desire to clean a primer pocket. in addition to being cheap, i'm also lazy. it's a combination that works for me.
tumblers are great and save a LOT of time cleaning cases, but are not necessary, they can be cleaned by hand. this is one area where my lazy side won out over my cheap side. i cleaned cases with steel wool for 3 years before getting my tumbler. now i would give up reloading before i gave up my tumbler.
as far as a bench, i started out on a old door laid across 2 saw horses. it works, but is not ideal. ideal would be a bench that is bolted to the floor or wall so it won't move or wobble. as far as size, i would think something as big as an average office desk would be good for a beginner.
it would probably be a good idea to invest in some sort of organizing system too. small parts bins on an old book shelf is what i use.
finally, my advice to you would be to start small. by only what you would need to reload a hundred rounds of one caliber. then after reading the manual and reloading the hundred round, ask yourself, "what do i need to make this easier/faster/more precise." you will save yourself lots of money on stuff you don't need or won't use. after all, you can use what's left of that $1,000 to buy another gun!"