The pic rotated upon upload. Should be 90deg clockwise.

Theres no drip cap which it should have. Did your window have nail fins?

siding is tyically butted to the casing in your case. I would have mitered the corners and prefer sloped sills.

Caulking has the potential to trap water in .

There are four windows with siding as in the picture. The windows do have nail fins. How problematic is butting the siding to the trim instead of the window casing? There is a about a 1/8" gap between the top and bottom trim pieces and the siding on all four windows. Also, the casing along the bottom of each window is arched a bit. Should that gap be covered? I will retrofit drip cap, thank you. Is there anything else to make these less likely to trap water?

Caulk is not mechanical flashing nor is it a substitute. Have him do a detail drawing and post it please.

I don't think my guy is going to be doing any drawings. At several points he asked me what I would like for him to do with regards to siding, trim, and so forth. I remind him he was the professional. Though I did have to step in when his idea was to cut siding into 6 inch strips and tack it around the window as opposed to using trim board. The windows are as described and the pic is a fair representation of all. I'll remove the top trim pieces and install flashing over the windows Any other suggestions? Thank you!

Here are closeups from one of the other windows

Didn’t realize the casing was ripped down siding, It should be 5/4 trim board to creat a reveal. I’d be most concerned about how the windows

were flashed . Not sure what siding that is but most companies have thorough details on installation sush as gapping , flashing , treatmens of end cuts. Seems like your the General contractor and you might have to lake the lead on this.

There are several things that could be done better here, but as far as your original question, no, there is nothing wrong with the siding butting up to the window trim as opposed to overlapping. In fact, it is preferred.

The other items of concern have been mentioend above (drip cap, trim boards are not thick enough to provide a clean caulk joint, the way that the trim boards are installed, etc). It doesn't strike me as a professional job.

I‘m a home owner that thought he was hiring someone experienced with window install and siding. I am taking the lead on this but im no expert so i came here, I stopped him from ripping siding to use as trim. He used 1x4 instead. The siding is Hardie. Cant do much about it overall but am addressing the windows Thanks!

I’d start with making sure the flashing is right. I see no point in moving foward until this is done, with the exception of removing the trim boards to see the flashing. I’d assume its done wrong if the ”handyman” did this part of the job as well.

They may be experienced with windows and siding, but not with doing it correctly based on these pictures and description. There isn't much here to suggest that this person is qualified or capable of getting this done right, with or without instruction.

With fibercement siding, a better trim board option would be a composite of some sort, 5/4" as opposed to 1x assuming that you will paint it instead of aluminum cladding.

The exterior walls are OSB with new tyvek. the Tyvek was cut so that it folded over the 2x4 framing (top/bottom/sides), the opening was lined with flashing tape and bow tied in the corners The windows were then installed by nailing the fins to the frame. No caulk used. Top tyvek behind fin, not flapped to the exterior.

Then 1/2” insulation foam board, furring strips, and hardie siding.

Most of that is wrong. WRB should be over the nail fin on head, not wrapped into the RO. Nail fins should be back-caulked except for the bottom.

Like I said, thats where you need to start. There are some good vids by Dupont and 3m and Ansco has there own vids as well. I would also look into how the tyvek was done.

Ok. It’s taken a minute but I’ve accepted that I will need to remove/reinstall my windows. I will post before and after pics. Damn.