How not to paint a wooden mailbox

As I painted this I kept coming up with ideas on how it would be easier, after I had just done it the hard way. So this will be more of a 'how NOT' to instead of a 'how to.' ;)
I've had my eye on this wooden mailbox at Joann for a long time now (retail $7.99, but I used my 40% coupon so it ended up being about $5), I knew I had to have it for a Valentine's Day decoration. My husband's mother is way into decorating for every holiday/season and it is from her that I truly got into it myself. It is from her that I got the tradition of everyone in the family decorating some kind of bag/box to be their Valentine's mailbox. Then everyone can make cards for one another and/or deliver treats to their 'mailbox' on Valentine's day.

This is them making their mailboxes last year

My original idea was to get 4 of these mailboxes, one for each one in our family, and to let everyone paint it themselves to replace the paper bag idea. However, I started to worry that my boys might not be happy with the paint job they did this year in another 5 years. Anyway, I ended up with one mailbox that I painted myself to be a decoration.

First I removed the flag, then started taping. If you have the blue painting tape on hand, use that by all means. Masking tape just barely does the job. What I wish I had done, was paint the whole body the lighter color pink, THEN tape just once to paint the darker pink

You can see I chose to do it the hard way.

To write our last name on the mailbox I just chose a font I liked, increased it to the desired size, printed it, and then cut it out. Then I taped it to the box, traced it, and then spent a LONG time very carefully painting it. It was at this point that I started to think of ModPodge. It would have been so much easier to modpodge the letters right onto the box. If you have a cricut (which I do! and I still didn't even think to use it), you can just cut the desired letters out on carstock and then modpodge those babies right on. It would be so much easier.

After I had it all painted I realized there was something bothering me about my color scheme - I had recreated a Victoria Secret bag. They are pink striped, just like this, with black lettering. Nice. If I had to do it over again, I would choose two red tones instead of pink.
That little cupid guy is just a diecut I had that I traced on and then painted. Over the next few weeks I will sneak little treats/crafts/goodies into the mailbox and then put the flag up for my guys to discover.