We're in the process of buying a stucco house built in 1930. It's around 1500 square feet and has finished attic space with fiberglass batts and vermiculte on the attic floor and f/g batts in between the roof rafters. The roof is about 10 years old and there is vinyl siding over furring strips covering the original stucco. The house appears to have a clay block frame under the stucco and is located in SE Pennsylvania. My question is where to start. We have some time before move in and could finance some significant improvements before moving in, but probably not a full deep energy retrofit. I've been reading about DER's for a year and dream of doing one someday, but I'm not sure how practical or affordable that would be. The siding is in need of replacement, which seems like perfect timing for some exterior insulation. But that raises questions about integrating with the roof which isn't in need of replacement. The attic space is currently finished, but doesn't meet building codes (only 6 ft tall in the center). I've considered making the attic storage space and pulling out the knee walls to allow for better air sealing and insulation, and possibly interfacing with some exterior insulation. We also plan to replace the current windows before moving in. Does that affect the decision to reside? In other words, is it better to reside and install windows simultaneously to ensure proper flashing and alignment of the wrb plane? I apologize if this is a broad, rambling question. I believe strongly in making this house better insulated and air sealed, and would like to develop a long term plan to achieving that goal. Thanks in advance.

Let's ramble a bit further, so that we're clear on what we are looking at:

Is the structural wall terra-cotta block or red brick, with the stucco applied directly to the block, or is there vented air gap between the stucco & block?

What is the stack-up between the block an the interior side finish surface?

What sort of exterior siding were you considering?

How deep are the roof overhangs (both eaves & rake of the roof, if different)?

Is there any existing window flashing?

What are your heating fuel options & heating system type?

Full basement foundation, crawlspace, or slab-on grade?