I think it is awesome to give a piece of furniture a new life. It is sometimes a bit daunting to take a paint brush to a piece made from genuine old timber but if you are going to get many more years of life and enjoyment out of it I think it is better than dumping it. I believe it shows your love. jbof4 I started with a heat gun to remove most of the many layers of paint, (some are easier than others to strip this way). Then I used an orbital sander and sanded and sanded and sanded. You might also try liquid paint stripper although I find this very messy. I believe you can also get them professionally stripped. Good luck with the resurrection, go for it what have you got to lose.

It looks to me like a lot of your boards [in the first picture] are cracked and need to be replaced. Notice cracks where the nails go through. I say this because my husband has had to replace a lot of boards like that on our deck over the years. After you replace them, sand the deck enough to allow a fresh coat of stain to be absorbed, and it should look new again.

I agree that you should take down the trellis but be aware that you'll probably need to extend your decking rail along that side in order to enclose the deck for building code purposes. If that's more of an expense than you're willing to incur right now, consider at least taking it down to the same height as the rest of your deck and putting a top railing across it. You could then put in some foundation plantings that would climb up and cover the fact that it runs in a different direction than the front of your deck. If I'm looking at it correctly, your gate gives you access to your front door from your drive way. Am I right? In that case, I think your gate should stay where it is. I agree with flair lighting that a new light is in order over your entry. If you like the idea of a motion light, they make decorative outdoor fixtures with motion lights built in. Your fence would definitely look nice painted a lighter color. Right now, as flair said, it's a bit unwelcoming. If you're painting your metal roof, take your house and trim colors from there to coordinate. You could definitely paint your scalloped trim a different color than the house. Matching it to whatever trim color you choose would look great. Do you use the steps from your deck to access your yard? If not, I would consider removing them and closing in that portion of the deck as well. If you do use them, I would add a hand rail for safety purposes. Congratulations on your new house and good luck with your project!

What is the rest of the house like? Would you like overflow sleeping areas or more storage? If you can't raise the floor (and the ceiling?) you might consider building in some comfortable seating/storage areas that use pillows/cushions and play up the multi-level idea and make it look intentional. Similar in concept to the stepped couch.