Replace windows or siding first?

[Chris Cogan]

I am planning to do some projects on a house hack that I have been in for about a year. This is a SFH with a detached garage apartment. I am looking to replace all the windows, siding and possibly add a wrap around porch. My question is what order should I do these projects? I have read some people say they would do windows before siding and vice versa.

[J Scott]

Windows first. Then siding.  Ideally at about the same time, so that you don't have any open penetrations.