Before you do any type of planning, get someone in there to make sure your foundation will support a second story. Some will, but, many will not. Once that is done, then, and only then, do you do any type of planning.

Hopefully materials costs and availability will get back to normal by next year. Do you plan to occupy the house while it's being worked on? If you do, be prepared for a major disruption. You may want to plan on a storage unit for 6 months. If you also want to renovate your existing house, you may be required to bring much of it up to current building codes, like electrical system and egress windows. Adding up can be a challenge.

I think we’re about 2 years out, if we actually do this.

We would not live here while it happened.

We would like to stay in our neighborhood, but lots our size (while not huge) are hard to find, or a builder has torn down the house and built lot line to lot line.

We're doing something similar now - adding about a master suite 500sf to a house originally built in 1951. Existing square footage is about 1850. Our house had 2 previous additions in the 1980s - full height second floor and then a one-story back addition a few years later. We're bumping up the back addition.

All I can say is find a great architect and structural engineer. Our architect is totally practical and has been working with our contractor every step of the way. The structural engineer has also been key even though I've never actually met him! Once demo started they found a lot of surprises about the framing and other issues that have required creative (and in some cases expensive) solutions.

You're smart to take your time; you can probably see from my history that I posted here a bunch before I really had a plan. I learned a lot from reading and occasionally asking advice from all the smart people on these forums. I have a million more questions now that I have to make all kinds of design decisions!

These sortss of projects almost always reveal a lot of expensive surprises. Be sure you have a contingency fund as part of your budget.

Good luck!

"Overwhelm me" is cute. I'm the type that thinks way ahead, and you could call it dreaming - I save money by planning 2nd floor bathroom over the 1st floor's...

Repeat of what others have already posted. Hire an experienced pro - be it a builder who specializes in older homes, a structural engineer, or a combination of both - and have them look at your house from the foundation up. We originally planned to add a second floor to our 1915 bungalow but after having the actual structure of our home investigated, the determination was that it was definitely not built to hold the weight. Now, it could have been done but we would have had to spend approximately $100,000 to completely redo the framing and support the foundation. We changed plans and went out the back to add the needed space. Yes, we lost some yard but I could not stomach that much of our budget going to structural changes. This process took months and months so if you think you are 2 years out, start now. Best of luck to you!

Also - look at your local building code relative to the space you expect to gain. In our city, you can only go up on 40% of the footprint of the house, so you might spend a ton of money to get minimal space. That might by why there are so many tear-downs in your neighborhood.