Well, scratch my fascia/soffit question. That would cost $5K. I can do a lot of painting for that much.

On the venting, I"m leaning towards a ridge vent + soffit vents. I can pretty easily put soffit vents in the underside of the porch ceiling, which connects to the attic. I'll need to cut holes in the trim on the back side of the house to vent that side of the roof.

Has anyone ever used attic windows as a vent? Like open them and just expose the screen?

This may be of help: https://www.hpdconsult.com/pros-and-cons-of-attic-windows/#Pros_and_Cons_of_Attic_Windows_Benefits_and_Cost_of_Attic_Windows_Types_of_Attic_Windows_Problems_with_Attic_Windows

I would spend the 5,000 and take care of the soffits and fascia. It will be well worth it. On that house, I wouldnt use a ridge vent. I would use roof vents (can put them on the back side of the house), and soffit vents. I would not use a window for a vent.

@cat_ky why do you recommend against a ridge vent? And by roof vents, do you mean those whirlybird things? I don't care for the look of those.

That era house did not have a ridge vent, and no, I dont mean a whirly bird, although they do a very good job, I mean a regular flat roof vent. Roofers install them all the time.

Update: The re-roof and porch rebuild is done. We did add the ridge vent, and now need to make a decision on the venting. We need soffit vents on the front and back of the house so we can draw the outside air in.

On the front, I'm thinking painted porch overhang, with horizontal soffit vents (the kind that look like HVAC return vent covers) over the gaps between the rafters, which are open into the attic.

Would it look funny to just have vented soffit on the rear of the house, and paint the exposed eaves around the rest of it?

Here's an illustration of what I'm thinking in the front.

Joe, the header is actually a steel I-beam, supported by those 4x4 posts on each of the pillars. The roofers applied the wood headers to the front of the steel beam to support the rafters. They were walking a tightrope of rafter notches vs. height of the porch roof vs. slope of the porch roof.

I do plan to trim out around the header to improve the aesthetics and make it more like the original.

Here's another view of the header on the porch.

And here are the rafters in the rear, where I'm thinking to just cut holes in the top plate and cover with soffit vents. Is that kosher?