I always book through Expedia as so far I've yet to find anyone cheaper. If you can try and stick to hotels in midtown as that's the easiest place to get everywhere from and if you are unsure about the saftey of places is without doubt the safest. Having said that NY is not like it used to be and in alot of ways is in fact safer than London now.
Do not be afraid to use the subway, it's clean, safe and very cheap.....cabs are very expensive and some cab drivers have been known to take tourists all over the place to get the fare up. The one good thing about cabs from JFK/Newark is that you can't be overcharged because the fare is fixed at $45 but they do add the toll charges which is around $3.50.
Try and fly into Newark if you can as it's much nicer airport and immigration there are nicer....LOL!!! It doesn't make a huge difference which you go into as far as distance from Manhattan.
I have just come back from a week in New York and stayed at a hotel called The Moderne, which was most disappointing (review will be forthcoming once added to the NY hotels). I have also stayed at The Pennsylvania, The Mansfield and The Helmsley Park Lane (see my review on this). The Pennsylvania is a two star budget hotel which is very reasonable (and HUGE), The Mansfield is another modern hotel and the rooms are small but very elegant (again awaiting hotel to be added). If you have a big budget then go for real style with The Plaza, the epitome of Manhattan luxury. It is due to shut in mid-April for 18 months for a $25 million overhaul
As far as shopping goes if you are going to be there for a reasonable time then I HIGHLY recommend a trip out to Woodbury Common which is the outlet village a bus ride out from Manhattan. The ticket is around $35 and the buses leave from Port Authority about twice an hour. They have Gucci, Prada, Chanel, Christian Dior, Tag Heuer, Off Saks Fifth Avenue and loads more. Have a look at their site http://www.premiumoutlets.com/outlets/outlet.asp?id=7 That tells you all the details on how to get there too
Ummmm what else..........Century 21 which is another huge discount department store stocking everything from upscale designer clothing to home goods is a must, it is on Cortlandt Street (on Broadway) subway where you can also visit the site of the Twin Towers which is directly behind the store. Also if you want to see the Statue of Liberty but don't want to pay the daft prices some the boat companies charge there is a FREE ferry across to Staten Island which gets you plenty close enough, it's quite windy out on deck so wrap up warm or in summer it's great to cool down! Walk as far down Broadway as you can and you get to the ferry. Once you have done C21 then I highly recommend walking back uptown along Broadway. You will walk through some great shopping areas and don't forget to stop by Pearl River Mart which is a great cheap Chinese store selling clothes and household goodies. If you are a designer clothing lover then be sure to check out the Soho Bloomingdale's on Broadway as well as Lounge, Atrium and Scoop which sell some great unique designer brands that are sold at huge premiums in England
As you keep walking along you will go past all the regular American stores like Victorias Secret, American Eagle etc and a really good fun store Urban Outfitters. You will eventually end up at Union Square which has a lovely market mostly selling food but still nice to have a look round. Once you get past Union Square it gets a little bit tacky with all the lights and shows but more good sightseeing stuff.
You must also go up the Empire State building for some awesome pictures of the city from the viewing floor. It is on Broadway and 33rd St and costs $13 to visit the viewing floor
I'm a huge fan of Serendipity 3 http://www.serendipity3.com/ which is a wonderfully Boho restaurant famous for it's celebrity visits and immortalised in the movie Serendipity. It is on east 60th St a couple of blocks from the midtown branch of Bloomingdales http://www.bloomingdales.com/. If you go to Bloomies make sure you go to the visitors centre (be sure to ask if you can't find it) and get your 10% off card. Alot of the department stores offer these cards and make the savings even greater!
Lastly don't forget all your purchases carry the New York state tax which at the moment is 8.625%
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