I have a older house (early 20th century) that has undergone numerous modifications.

I recently replaced some of the windows and sure could use help.

The existing siding around some windows is multilayed:  The original sheathing (3/4″ pine boards), then a black tar-like paper, then what looks like an asphalt-based siding, then furing strips, then what looks like a cement-based fake brick siding.

Around other windows has a vinyl siding later over the asphalt-based siding.

As you can see in the pictures, there are substantial gaps around the windows where siding is now missing.

What should I do?

Of course, I’d like to rip all the siding off, down to the sheathing, but I don’t think that is in the budget now.  I estimate about 5000 sq-ft of siding (with lots of corners).

Do I have options for the short term?

Thank you.