Shipping miscellaneous items to the DR

I'm back in the US for a short visit and went a little crazy with my shopping.  I had a long shopping list to start with when I left the DR, but anyway...

I booked my flight First Class on American Airlines because I thought First Class could check in a 3rd suitcase for a small fee.  Nope.  It's $200 for the 3rd suitcase as of Feb 2024 (I didn't think it was $200 when I booked, but whatever).  FYI for anyone thinking of doing this same thing.

I have a shipping account with EPS, so I'm just going to ship stuff to myself in boxes.  No problem.  It'll cost less this way, I think. 

I know I have to include an inventory of the contents in the box. 

So here are my questions:

1. How detailed should this list be?  I mean, I have LOTS of little things in there.  Some big things, but also lots of little things.  Do I need to list each item and their individual value, or can I create a collective group for similar items?  Example, I have multiple 'household' type items.  Can I list 'Household accessories' with a dollar value for that group, then list each item individually as a line item but without the dollar value for each item? 
2. Should new items be removed from their packaging so that they don't look new?  For example, I bought some beach towel clips, to hold your beach towel to your chair.  They're still on the cardboard card from the store.
3. I know there's a $200 limit on items shipped.  If the value is over $200, then you pay taxes or something, right?  So, if I'm shipping multiple items in a box, would that $200 limit apply to the whole box, or just to an individual item?  Do I need to keep the total value of each box under $200? 
4. Will Customs go through every item in the box to verify my inventory list against the contents?  I have some towels and clothes packed in those vacuum-sealed bags to take up less space.  If they open those, they'll never get them resealed and vacuumed.
5. I know EPS charges extra for larger items, so I'm trying to use multiple small boxes.  Should I limit how many boxes I send in one go?  Would multiple boxes send up a flag to Customs or something?  I'm not shipping anything illegal, but I don't want to cause unnecessary trouble for myself there.  Right now, I have one medium box (18x18x16) and one small box (17x11x13) but thinking I might need another small box (still trying to cram as much as I can into a suitcase so we'll see).

Thanks for any advice and info, and I hope someone else can find this beneficial in the future.