I applaud your 'getting back to vinyl' reasons. You are an excellent candidate. If you read similar threads, and more respond to this one, you will get a LOT of advice on what the best way to spend your money is.
My most important advice is: don't worry about getting it perfect, because you won't. Vinyl can be a very slippery slope and I don't think that's where you want to go. Instead, think about how to get good bang for your buck and how to enjoy yourself because that is what your quest is about. If enjoying yourself means getting a refurbed turntable from the 50s because that's what your Dad had, so be it. If it means being able to play all your records (monos, 78s, stereos, etc) on the same turntable and arm with just a flick of a switch or a changeout of headshell to make the jump from mono to stereo, then make sure you can do that. If it means having autolift at the end of the record because you want it, go for it. If you want a transcriptor because they look oh so cool, well, that's what it has to be.
To start, I think a used VPI 16.5 record cleaning machine is the way to spend some of it. Or you could go for a nitty gritty which is less. Add a carbon fiber brush and a stylus brush and you'll be fine (for anyone with good hands, I also think a $2 block of Mr Clean Magic Eraser is an almost indispensable tool for cart-cleaning (thanks Doug! we all owe you one for that!)).
I agree with Daverz on the 'used preamp with phono stage' as you can get some great deals. If you have lots of OLD records (pre-1950), then you might consider an old pre which had the ability to change curve a bit. There was recently listed an Accuphase C-240 preamp which is quite decent in its own right, has an excellent phono stage (with two phono inputs) with MC headamp, has controls allowing one to change rolloff/turnover points on the equalization curve (i.e. allows you to set equalization appropriate for the record label because different labels used different curves when they made their records). It was in the lower half of the $1k-1.5k range. Stonking bargain if you ask me. There are others out there like that.
A lot of people think putting a $1500 cart on a $1000 table into a $500 stage is appropriate. I don't. I have consistently found that cheap carts on better tables into better stages will beat great carts on cheap tables into cheap stages. You can get great MM carts, vintage or new, for a few to several hundred dollars.
I would personally suggest you post a separate thread asking if someone in your area (put your area in the title) has a good belt drive or direct drive or idler system to allow you to show up with a few records for a listening session. Get a grip on which you like (belt vs DD/idler). Go from there. In your price range, they are different.
If you like belt, VPI and their arms should be good choices in your zone. If you like DD/idler, then I would go for someone's refurbished DD/idler in a heavy plinth with armboard which allows you to mount arm of your choice. This could be a Lenco idler, a Technics SP10Mk2, a Denon/Pioneer/Sony/Yamaha/etc table. If you buy a table without an arm built-in, an arm like the Micro Seiki MA-505 would be an excellent choice - great-sounding, quite flexible with carts, and not a lot of dough.
Isolation vs coupling is a great debate. In MY system and MY environment, isolation is appropriate. If you have non-concrete slab floors, or you live in an urban area not too far from the street, or you live in an area where the ground has tremors, it probably is for you too. I personally would suggest buying little magnetic floating platforms (look at Clearaudio's for an idea, then buy cheaper ones) or something like a used lab equipment isolation platform off ebay - passive is fine (sometimes they go for dirt cheap). If you can control the levelling, you could try an inner tube under your platform (i.e. table on wood block on inner tube on your rack. Use a larger diameter inner tube than a bike racing wheel and don't fill it too full. You want the whole thing to be soft, not hard.
And by all means, continue asking questions if you have them. If you keep the thread alive, it will show up on the list and people will respond.
Good Luck!