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iPhone
Locked version:
If you have a Verizon, AT&T, or Sprint account, the cheapest method is usually to join installment-plan promotions at major retailers. These are generally promotions where phones bought on installment through the three big carriers come with gift cards. For example, Walmart’s Black Friday offer gave $300 in gift cards (ended):
After the installment plan is activated, you can use an AMEX Offer to pay your phone bill and lower the monthly payment. AMEX often runs offers for paying bills at 80%-90%, so each monthly installment can also be reduced by 10%-20%, making the phone very affordable.
Note: iPhones bought through carriers or big third-party stores are locked (Verizon is the exception—Verizon models unlock once you activate with Verizon). Check each carrier’s policy for unlocking details.
Unlocked version:
The simplest and most reliable way is to buy directly from Apple.com or an Apple Store. Devices bought at Apple for full payment are unlocked, regardless of carrier. For iPhone X, different carriers support different bands. The Verizon and Sprint versions are more compatible nationwide; until a SIM-free version launches, the Verizon or Sprint version is recommended. iPhone 8 can be bought as a SIM-free model and is fully unlocked. Paying in full with a credit card also gives you extra benefits such as damage insurance and extended warranty coverage.
Another way to save is buying on eBay. Only buy from big eBay sellers. The "daily deal" listings are from big sellers, and you can search at https://www.ebay.com/deals. Large-seller iPhones are generally fine, and they come with official Apple warranty—I’m currently using one myself. The price can be at or even slightly below Apple list price. Combined with eBay buck offers and tax-free deals, it can be hundreds of dollars cheaper than buying at Apple’s official site. iPhone X eBay daily deals have shown up a few times, and they sold out quickly. Latest listing: https://www.ebay.com/itm/Apple-iPhone-X-256GB-GSM-Unlocked-USA-Model-Apple-Warranty-BRAND-NEW/162767889044?rmvSB=true.
Summary:
If you plan to use it in the U.S., use one of the three carriers with AMEX OFFERs. (Carrier account setup needs HP.)
If you are bringing it back overseas, Apple’s official website is recommended first, then eBay (needs to act fast).
iPad
iPad mini:
Currently the only one on sale is the iPad mini 4 128GB version. List price is $399; Best Buy has more frequent discounts, with several previous deals at $300 and $275. If you missed them, you can wait and try again. 12.7~9 Best Buy iPad mini 4 $275, 12.10~12.16 Target $300
iPad 2017:
This is the budget iPad, with list price $329 (32GB). Since launch it has been slowly discounting; the current lowest price is $249 at various stores during Black Friday. Best Buy is still selling it at 279. There has been news that Apple will release an even cheaper iPad (around $250) next year.
iPad Pro:
The current models are 10.5 and 12.9 inches, with list prices of $649 and $799 (64GB). The lowest Black Friday price for the 10.5-inch was Sam’s Club at $499, and it’s not easy to score. Best Buy has had two deals at $525. The 12.9-inch model can get up to $200 off.
Summary:
iPad is not worth buying at Apple’s official site. Retailers discount it a lot. Best Buy has frequent discounts, and stores like Target and Walmart usually run deals around year-end holidays.
Macbook
Best Buy is the top pick. Every summer, Best Buy runs student discounts on MacBook, saving $100-150, which can be stacked with other deals. MacBook Air and cheaper MacBook Pro models can save $200-300. You can register for student discounts at https://www.bestbuy.com/site/misc/back-to-school/pcmcat334100050000.c?id=pcmcat334100050000, which sends one discount per month. No edu email is needed, and Best Buy has MacBook coupons in the summer.
Apple’s official site also has student discounts in summer. Lately they’ve been discounting and offering Beats headphones. This summer, a MacBook Air 128G with Beats Solo 3 for $850 was very good value.
eBay daily deals often have MacBook Air and budget MacBook Pro deals, sometimes even cheaper than Best Buy. Combined with tax-free checkout and eBay bucks, they can be excellent deals. Pick the big sellers in daily deals; those come with official Apple warranty.
The current lowest price for the latest MacBook Air 128g is around $750, and the MacBook Pro 128G is around $1,100.
Apple Watch
Currently, the main models on sale are Series 1 and the latest Series 3. There are many stores selling Apple Watch; besides Best Buy and Target, most department stores also carry it. You can fully leverage department-store gift cards and high-cashback (rebate) sites for deep discounts (Apple products may be excluded).
The lowest price for Series 1 38mm is now around $180, and Series 3 has not been discounted much.
If you want to buy full-price Series 3, Kohl's is recommended. Pairing low-price Kohl's gift cards with Kohl's Cash promotions can make it very affordable. For example, a 42mm model for $359 can get 70 Kohl's cash, worth about $50.