Fellow frugalite here, and man, is it hard to break the habit of agonising over every purchase. Took me nearly 20 years in tech before I convinced myself I could justify just buying a new laptop every 5 years, and not sit around waiting for things to compile on the old one - and thats an item that is both essential to my work and also tax deductible. The agonising is even worse with items that are technically non-essential (but would make life better)