Hi Expat,
I do this all the time. I live in NY and my wife's family lives in Santo Domingo. We send down iPads, iPhones and laptops that we buy off of eBay (buy you could send anything). What you need to ensure is that each shipment is less than $200 cumulative value. So for example, I can send down (2) iPad 2's quoting them as a used value of $9 each and I don't pay import taxes or say, a Dell or Lenovo laptop that's a year or two old (say, with an i5 processor, 4 Gb RAM, 15" LCD screen etc.) quoted at $200. TV's would be the same. The key is that whatever tech you send, you only pay taxes if the current value is greater than $200.
So, here's what I do paperwork-wise and it seems to work well. I've never had a shipment held, delayed or otherwise questioned. I include in a clear envelope on the outside of the box (you know the type a FEDEX label would go in):
#1. An invoice that I type up in Microsoft Word with a line item description of each item I'm sending and a price. I've included an example below of one I used for sending an iPad2 (note, I've put the links in as both a link and an image link, not sure which will work)
https://1drv.ms/i/s!Aiq5GmzBb9XX5zfnLfxGlhW2zpC5
#2. Then I send something to support the price I put in the invoice. Note, this step is probably optional however I do it so it isn't questioned how I got the used price valuation. Note I tend to go to eBay and find the item I'm sending and print one of the postings that are listed at the time in order to show relative value. See link(s) below for an example of this.
https://1drv.ms/i/s!Aiq5GmzBb9XX5zhdYpLif69kJhkr
#3. That's it. I use a courier in Miami so I FedEx Ground the item to the courier with the two items above, the invoice and price support document in a plastic envelope on the outside of the box so when it hits the DR, they can examine it. Note that for good measure, I also include a copy of the two docs inside the box as well. I hope they never open the box because I know that it means I'll probably never see the items again! LOL! Hope this helps
-Jim