The first picture is ours, the second is an example I pulled of what I think it should look like.

Aw, it's a cutie and has so much potential.

I feel like there should be a primer on "I bought an old house, now what do I do" but definitely make sure your major systems are operating and sound first. Plumbing, electrical, and HVAC can eat up a lot of cash.

For the exterior, read this guys' thread, there's a lot of info in there about selecting materials.

https://www.houzz.com/discussions/6027866/restoring-a-hulley-house-advice-needed#

Thanks! Yes we had all that checked on in the inspection and have thankfully just a few systems level repairs to make. 🙏

It looks to me like a pretty plain box with roof that someone added a porch to. If you want to make it into something like your inspiration pic, that's your choice, but it's unlikely to be a restoration of former glory.

You can do research, town historical societies and old records are a place to start. We found the architect's original design for our 100 year old house. Also look for historicasl records of additions. If it was fairly modern, it might have needed a permit.

Have you hunted for historical photos of your house in its original state when built? Check into your city's assessor, building and tax records -- here in the other Portland, we have access to a great database of tax records from the early 1920's that includes contemporary photos of each address, and it's a real goldmine for details. You might find the most gratification in restoring it to look similar to its original design. Have fun and best of luck!