Should It Stay or Should It Go? (A new feature)

I am seriously driving myself nuts about what I should keep and what should go.... I should mention I went through this moving 5 years ago and got rid of lots of things I wish I hadn't: years of Christmas, Halloween, and Easter Martha Stewart Magazines..... a coffee table I could use right now, and some other things. Overall, it felt great to lighten up. But now I don't want to bring unnessary clutter into my new home, although I do need to buy some furniture-- I am short 2 sofas-- so I do need $$$ to buy new furn for my formal LR and Den.....

I decided that since I am in the process of PURGING prior to my move, that I will post the items I am seriously thinking of getting rid of at garage sale in 2 weeks. I will post the pics with a short description, then you tell me if I should get rid of it. Maybe you'll have some ideas on how to transform them also (if I keep em?)

Outdoor Set: I only paid 100 bucks for this at Big Lots... the cushions really need recovering, but overall its an OK set- but it is NOT comfortable... I am envisioning more of a "ooo this is comfortable" outdoor set- but those cost in the 1200.00 range... whacha think? Stay or go?

Pier One rattan chair: Also NOT comfortable... its just OK with a lumbar pillow... but I kinda like the style... but I will have to restain some of the frayed rattan parts... overall not in love with this... Stay or Go?

Iron Rose Shelf-Thingy: I guess I bought this when I almost went Shabby-Chic, then I remembered a man shares my house--how could I ask my burly, manly he-man to live surrounded in ruffles and crystals and pastel colors? But can I paint it? What can I use it for? It travels room to room in search of a home and a use. Stay or Go?

Daughter's Dresser: I love the style of this, but one drawer doesn't close all the way and my daughter says it looks "dirty" (she doesn't "get" the distressed look!) I had dreams of putting it in my foyer but me thinks me style has gone more modern than this now, although you can successfully mix pieces in I suppose... Stay or Go?

3 cheapy side tables: Got these with my coupon at Michaels and I think they cost me all of 8 bucks for all 3. Maybe I can paint them (ORB?) and mosaic the tops? Maybe for outdoors? Or bathroom? They fold which is kinda nice- but their surface is so tiny they really barely hold a glass of iced tea. Stay or Go?

(yes, there are 3 of these...ones in my teenager's room covered in....stuff.....)

Shelf I have had FOREVER...in my linen closet hidden away: OK, I have had this since before I married-- 15 years! I was in love with these little carved wood folk-art shelves you'd find everywhere in antique malls... used to have 3 others that have since gone bye bye. Everyplace I have been , he just ends up stuffed away because I can't find a use for him.. Stay or Go?

CD Unit: I am really toying with the idea of painting this, with big numbers on the drawers, and using it in my kitchen as a spice storage or something.. I really, really like the way its made, its all wood construction and solid. But will I do it? That also means I get rid of the CDs in it too- but I am a big IPod failure... I really don't like earphones.....I just end up listening to talk radio in the car and silence is golden in the house when I am alone... unless I listen to Maria Callas right off YouTube... soooo... Stay or Go?

Birdhouse: I know, I know...But I am so over white and blue beach house..... but Stay or Go?

2 Office Armoires: these were cheap on clearance at OfficeMax. Currently one houses my son's stuff & TV, the other I tried, but failed, at re-inventing as a "Homework Station"... I organized homework supplies, had a cubby for each kid, but it didn't catch on.. partially because it lacked proper lighting... If it stays its definitely getting painted.. Stay or Go?

Daughter's hutch and desk: This was free. Maybe my other daughter can use it, she'll need a desk, but their rooms are small in the new house... how can I make it current? Stay or Go?

Thank you--suggestions and ideas appreciated!!!!!!!!!!!!!!!!