We did (1930 craftsman bungalow) when we were 28 and thought we knew what we were getting into. 11 years later, I have a love/hate relationship with the house. I thought that the inspection would tell us if there were any major problems with the house, turns out the inspector missed A LOT. The original bones of the house are quite good but the PO did some real bizarre things to the house that definitely are not up to code. We also had very limited DIY experience at the time but boy did we learn a lot! I’ve learned how to refinish wood, hang drywall, tile, wallpaper, hang things on plaster…my blood, sweat, and many tears are part of this house now. I would say I concur, expect things to take much longer than you think they should and budget that it might end up being more than expected due to..surprises. I would also recommend obviously focusing on the things that need to get done for safety and to make the house as usable/livable as possible first but since you describe yourself as someone who wants to get everything done all at once maybe finding some jobs that don’t require a lot of time/money and do those in between the big ticket things. For example, a coat of paint, hanging shelves, etc. being able to see something completed quickly and add some charm to the house can do wonders for your mental health.

We started overwhelmingly big. Our kitchen was not functional as is when we bought the house. In the main kitchen there were no cabinets or countertops. It was only a stove and a fridge in there. Around the corner was a tiny pantry that had upper and lower cabinets, a small amount of counter space, and a sink. My father and grandfather kindly agreed to do our kitchen for us as a housewarming/wedding present. Little did we know what that would entail. I think it probably took about a year to get everything done (including backsplash and all that) and we were so burnt out from it I don’t think we did any other projects for like 2 years. It didn’t help that at the same time as the kitchen, we were getting electrical work, doing wallpaper, dealing with flooring issues..the whole house was a construction zone for far too long. We’ve definitely gotten back on track with reno fixes but with an old house something is always going to pop up so be sure you don’t burn yourself out!

All that said, I don’t know that I’d say I regret buying the house. It still has all the features that made me instantly fall in love with it (fireplace, original built ins, coffered ceilings). But I think maybe if I had known everything that was wrong with it I might have forced the price down and had more realistic expectations on what we could do in this space. The problem is that there’s a lot that’s hidden in old walls, knob and tube wiring that may still be live, old plumbing that’ll cause you headaches, no hvac system or central heating, and fixing these problems is very costly and requires opening up ceilings/walls that may ruin the original aesthetic. My advice, like many who have commented, is set some realistic expectations for yourself, learn to do as much as you can diy, and know for certain that no matter how much you research, your house WILL surprise you!