Preparation outside is just like preparation inside: it's 80% of the work of painting. Yes, you can leave securely stuck on paint on. You have to remove the rest (ultraviolet light, heat, scrape, sand, or chemical peel), and then sand or scrape down the edges where remaining paint and bare wood meet. You should also plan on washing the painted surfaces first, as they need to be clean in order to adhere to the new paint. (Warm water mixed with a stiffish dose of Clorox and some TSP, applied with a scrub brush -some elbow grease required - and then rinsed off with a garden hose, not a pressure washer.) If the previous paint is still shiny, you will need to de-gloss it chemically or sand it lightly. (Feel free to curse previous paint jobs that left you with shiny paint in that case.) Then you have to make any repairs to dings; deal with any visible nail heads, etc. If some of the wood is really old and dried out, you may need an undercoat of linseed oil/turps mix. Then pre-prime the repairs and nail heads, prime the whole shebang and then put on two coats of the finish color(s). Oh, yeah, don't forget to check your caulking and flashing and replace what needs attention post prime, pre-finish coat. I have to believe you live somewhere south of the Mason Dixon line, because where I am, tardy painters are working under lights and praying for dry warm days in order to get their projects completed before it's too late. And since you described your house as a Craftsman, it's important to determine if you are dealing with lead paint before you do anything that creates lead vapors, dust or chips. It certainly is possible to do your house yourself, but it's not a small job and you will need good ladders and scaffolding, lots of tarps, a lot of free time, etc. HTH Molly~

Thanks, squirrelheaven, I am thrilled. Yep, the door was accidentally painted semi gloss white like the trim instead of the artichoke on the shutters. Also, the shutters on the far left of the house as you look at it are too short for the windows. I assumed all the windows except for the new ones on the side were the same size-but the ones on the second story to the left are about 6" taller. Oh well, it can't be that bad if you eagle eyed ladies missed it. Yeah, the weird shutter in the middle-can't really do anything about it except space the gap between the two windows... My neighbor says to leave the door white and just put a big green wreath on the door (if I wasn't planning on selling it that door would be pumpkin tomorrow!!!LOL) I'm thinking in my next house (maybe next year) I want to do a pumpkin colored dining room. My husband says that's fine as long as I hire a guy to paint because I'm the messiest painter *ever*.

Could you do something that looked like an old fashioned basement bulkhead that would be open instead of having doors on it? In your location it might still be odd to have something like that on the front, but it could at least possibly look original. In my city most of the houses are row houses and many of the 18th or early 19th century houses have a basement bulkhead on the front of the house next to the stoop. Some of the houses retain the old bulkhead with doors, but a good proportion have converted the bulkhead so that there is a large window in the basement wall and the top of the bulkhead is open, acting as a skylight of sorts for the basement. In my location most of these are topped with metal bars or another window like Plexiglas because they are on the sidewalk and people could fall in. However in your yard you might be able to keep this open. I don't know how this would look without seeing a picture, but in general the more it looks like it could be a part of the house, the better, even if it would be an unusual location for a basement entry .

What type of windows, full replacements or inserts? Full replacements, you do the windows first as the siding needs to be pulled back and the trim most likely removed. Inserts, fit in the existing frame and the frame gets wrapped with aluminum typically so it does not matter as much.