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We are currently tackling the same project at our two-bedroom townhouse. We are painting everything (trim and walls) and decided to start with trim, and then do walls so that we can be a little messy painting the trim. We did test sections both ways and it was by far easier taping off the trim than it was the walls.

I hear you about the ridiculous cost--I'm contemplating leaving the stairwell it's current beige color because I can't figure out how to get up to the very top without a crazy-dangerous ladder situation. Perhaps it won't seem so dingy once the trim and other walls are painted!!

Painting is all about prep work.. The actual painting part doesn't take long, but the prep will take you as long if not longer than painting!

Clean surfaces, patching any holes or dents, taping off, tarps/drop cloths. Trim is tedious and needs to be done with just a brush. I'd google some painting tips if you've never done it before so you can learn the techniques, materials needed etc.

We painted our entire house. Some areas look great.. others when we got tired you can tell aren't as good. Luckily they are in areas that need to be repainted or reno'd but take your time!

@LBee: Your #1 made me LOL

Painting is so easy, seriously! My mom and I are always painting something in her house or mine. Get good painters tape, make sure you press firmly on it. Patch any holes. Get a brush, get a roller, paint.

We painted all our trim a few years ago, and it was doable for sure. It takes time and patience, but you can do one room at a time.

1. Move all stuff away from the walls
2. Sweep and mop or vacuum the floors (you don't want floor gunk to get stuck to the trim, and you will be scooting around on the floor as you go
3. Wash the trim with soap and water
4. Patch any holes with caulking and let dry
5. Paint! You don't need to tape if you use a smaller brush and are careful. Wipe up any drips with a damp cloth as you go.

Good luck!

Good brushes. Good brushes make a difference.

Spend the time to tape everything. It's annoying AF sometimes and you are like let's get this over with already but this is the most important part (IMO). Painting is like 90% prep and 10% actual painting.

YouTube and Pinterest have great tutorials and videos

Protect your floors.

Take a day off work and just do it all. I've tried the "here and there" method and it's a huge PITA to clean up and then get everything back out. Just take a day off, take your kids to school, turn on the radio and get to work!

Don't try to touch up, unless it's been done VERY recently and you know FOR SURE what paint was used. Our painters did a patch to show me just how mismatched whites can be, and it is baaaaa-aad! So based on this, I'd say consider it an all-or-nothing job within a room/line of eyesight.

Skip the tape and learn the cutting-in technique to go without it. DH is much better at this than I am; I'm too impatient. Putting up tape adds so much time to the project.

Have you tried a magic eraser before undertaking painting trim?

If any of the floors are carpeted, I would skip it, honestly. You're going to have to use a palette knife to get a good line and then you risk fibers in the wet paint.

@Anagram: I paint on my own all the time

Advice: The night before empty the pantry and wipe down the walls - get paint out and brushes and a rag- that way come the morning you are ready to go! Put on music and dive in!

For the trim I like to use Behr white in semi-gloss - makes wiping them down so much easier than an eggshell would be. The night before use hot soapy water and wipe them down.

For rooms - I don't use tape - I use the Wooster brush for cutting in and just take my time - I do 2 coats of cutting in and then 2 coats of paint. Have a ladder handy and all window coverings down the night before -

As for holes that's only if you aren't putting up the same exact thing or you got a ding from something heavy hitting the wall

Good luck!

So if you are painting trim you shouldn't have any patching to do. Just rough it up a little with sand paper. Try to wear down any old runs. And if you are repainting all of it, you just need to match it to itself. Patching is usually on wall where there are holes, or bad drywall jobs. Our walls were a mess so we had lots to fix, but our trim didn't need too much work. If there is any exposed wood, you can paint it with primer first.

We painted our crown molding on our ceiling bright white, then realized it made our ceiling look terrible! So we cut in all our ceiling tiles with the paint the owners had left (marked ceiling). But we ran out. So we bought more ceiling paint and it didn't match exactly, even though it was white. We then had to roll the whole thing and redo all the edges next to the crown molding. It looked great when we were done, but was more work than we anticipated.

Just doing trim doesn't involve moving and covering as much, but it is very time consuming if you are being neat.

Oh and there is some technique involved so do watch some videos, or see if someone would be willing to come help you start.

ETA-just saw your plan. I find painting trim is easiet to get done little at a time because there is way less prep involved. I tend to do a piece during nap time- triple window one day, stairs the next day...

These are one of the best things I discovered in two summers working for a painter.
https://www.amazon.com/dp/B001CSPGJY/ref=cm_sw_r_cp_awdb_XcUYybSMDD1KT

And these:
https://www.amazon.com/gp/aw/d/B00GS9TJ90/ref=mp_s_a_1_3?ie=UTF8&qid=1489690905&sr=8-3&pi=AC_SX236_SY340_FMwebp_QL65&keywords=paint+can+pour+spout&dpPl=1&dpID=31SxUz7xiLL&ref=plSrch#

They are both cheap and available wherever you buy paint.

@Anagram: just trim, you can totally do on your own, if the nanny has the kids. DH and I have been tackling most of our paint projects together, with no child care, so snippets during nap and after bedtime. And yes, if you are doing all the trim you don't have to worry about matching the white, but painting fresh white paint over already white will be much easier than if the trim was a different color.

What color are your walls? The lighter they are, the more forgiving it will be if you go past the line here and there.

Personally I would start by taping most things unless you have a really steady hand. As you get more comfortable you can stop taping. For me, after painting a bunch of rooms and having a painting background, I still like to tape over baseboards and in hard to reach corners. We don't have crown molding (yet) so that hasn't come into play. And I've only done the outside window trim but nothing on the windows themselves since we are replacing them.

Most of these comments are fabulous advice. Husband and I painted our condo together a few years ago...it did not go well - it caused a lot of unnecessary hostility (and we almost never disagree or fight)!

Fast forward to this past September....we purchase our (hopefully) forever home about 3x the size of the 2 bedroom condo we painfully painted together. Our house is COVERED in wallpaper. My husband HATES taking down wall paper and I HATE painting (he is REALLY good at painting!). We made a deal, I take down wall paper and he paints. We have divided the tasks that I also do the cleaning of walls, trim, doors, and taping of low parts (currently pregnant). He does all of the painting and high prep work.

This arrangement is working out wonderfully for us! So much smoother this time around. Our expectations were set in the beginning and it has made process very pleasant. My husband is currently painting all of the trim, doors, ceilings, and walls in the entire house. 6 months in and he is about half done with the house!

In my experience - if you are even considering painting the trim...do it all WALLS, TRIM, & CEILINGS! It is more work and more $$ but it feels so fresh and clean after it is all complete.

A few bits of advice....
-set realistic time expectations, try not to rush and do a complete job (nothing worse than having to go back bc it turned out bad bc you rushed!)
-Do not leave the tape on a freshly painted surface for more than a day or two. (ESPECIALLY if it is in a bathroom or high moisture area).
-label all paint cans with area and what they are
-keep your sheens correct.
-if you are having kids (or have them or pets) make all surfaces washable, but dont go too high with the sheen or it shows ALL the imperfections.

HAPPY PAINTING!

@KITTENONTHEWAY: do you have any advice on sheen?

We're also going to be painting so this thread has been greAt!