You need to remove all of the exterior siding and trim, fix the water damage, then re-side with a quality product like Hardieplank. Use composite trim that won't rot. Pay a lot of attention to the flashing and tyvek.

Thank you, that is what we are doing and using LP smart side we are tying to figure out what brickmold - for lack of better terms to use what it should look like. That is my question

I would use their 5/4" x 4 flat boards as the window casing, your appears to be that is real wood currently.

Some things to understand about exterior siding:

1. The siding is the first water shedding surface - but it's not the final. There should be Tyvek or similar (Tyvek is actually superior to most) that is the drainage plane.

2. Caulk should not be relied upon to maintain waterproofing. It will always dry, crack, etc.

So, the answer to your brick issue:

I would use L shaped flashing from the wall at the brick line to a point completely covering the gap between the brick and the wall plus 3/4" or more. I'd seal the underside of that flashing with clear silicone caulk to the brick to prevent water going under the flashing. Then Tyvek on the walls to overlap the flashing. The brickmould trim would go over the top of the L flashing - hiding most of it - and Z flashing would be integrated into that. The siding and the flashing is the first water shedding and the Tyvek and the next layer of flashing is the final drainage plane.

You have a Palladian window upstairs. Google it to see good examples. Done properly - it shouldn't look like discrete units - it should hold together. The installers didn't really build it that way - so I'm not sure how that will work if you make the trim wider. Sketch it out to scale and see how it looks with wider trim.

Thank you This is that masonite omniboard siding that was recalled, which we never received notice on so thats special. Thank you for the term on the windows and suggestion on the moulding

using LP smart side

I encourage you to revisit that decision. LP Smart Side is OSB (oriented strand board) with a fancy name. Maybe OK if you live somewhere with less than 5" annual rainfall. Otherwise, I would strike it off the list of potential siding material.

@ci_lantro thank you for the thought, ill give you another back. Our rental in IL was done in 2008 with this product, to this day, zero issues What would you suggest?

My brother had a very similar window set-up to yours in his family room. When he re-sided, he removed the Palladian window. It looks much better, updated, and the room still gets plenty of light.

Good question, Amy Gohl.

I'm researching what to use myself. I have a really tricky spot & have ruled out Smart Side. (Central Wisconsin). Have not decided.

What I don't like about SS on your house is the dormer penetrating the roof and looking at the spots where the Masonite has obviously failed on the face of the dormer. Those failure highlight areas of most vulnerability and like tell you future potential trouble spots with Smart Side.

Maybe steel or vinyl? Hardi?

I agree with previous suggestions to remove the Palladian window and to trim the 3 dormer windows as one ganged window vs 3 separate windows.

We are not removing the windows, it would cause issues on the interior . the masonite siding has been recalled that part of why it failed, but we are putting full trim between the taller windows, and a larger piece above the windows between the half circle window @ci_lantro, i would urge you yo rethink the lp its a superior product to Hardi i would never do vinyl as hail would make is look like a golf ball. im from Burlington and our rental is in Johnsburg IL That house has lp and no issues it sits across from a lake and you know the weather up there My husband did it right, painted the butt ends, or even ive taped at some points This house was built in 1996 so its due

I would go with hardi, way before LP. I have seen that fail many times. It is most definitely not superior to Hardi, however, since you have your mind set on LP, then go for it.

Amy has decided.

Anyone else who is considering using LP Smart Side should look at this video of 8 YO siding in rural Illinois:

LP Smart Side Fail

@ci_lantro can you delete this from my thread please- its 5 yeara old Every product will have something wrong with it We have our house in a rural town, across from the chain of lakes installed for over 10 years We have guys here is Oklahoma that sell both products that say they have issues with Hardie board I just wanted help with the brick to lap issue to be honest