I can't advise you about the chest freezer, but I do use a spreadsheet to track food in my upright and kitchen It has 5 tabs: Prepared Foods, Prepped Ingredients, Meat & Fish, Fruit & Vegetables, and Grains & Legumes. Those are divided into sections containing columns; e.g. in the Prepared Foods I have "Frozen Dinners, Cooked Meats, and Desserts." Meat & Fish has "Poultry, Seafood, Beef, Pork." Within these larger columns are the expected "Name, Date, Measure, Quantity and also K or B to indicate kitchen or basement.
Once the spreadsheet was set up, it became relatively simple to keep it up - just a few words typed in - but I have to keep after myself to do it. Just finished off an entry of "cooked chicken" today, and I did remember to delete it.
The main challenge I am facing is the "Prepped ingredients" page. I do have an ambition to work in these sauces and partially cooked mixes into meals, but haven't figured out how to do that smoothly. For example, I have some chopped, cooked, frozen bacon that you'd think would be easy enough to incorporate in something, but I keep failing to do so.