In the past I would buy one pair and wear them until they fell apart. Sure it worked great for expenses, but Murphy's Law is a pain. Always failed at an inconvenient time. I finally found a pair I liked. Bought a set in 2020, got them broke in. Bought a set in 2021, broke them in and swapped the pair in and out during the season.
I'll buy a third pair this next year and break in. I usually wear out boots every three years for hunting, but I've gotten to where I wear them year round, nearly daily. So, I figure with three boots in the rotation, if a pair wears out the GoreTex or has a catastrophic failure, I've still got two pair good to go.
Not the least expensive way to go, but I prioritize boots as I use the heck out of them and they are an investment in comfort. When I find some I like, I want to be well stocked and not have to be concerned about what ifs in the field.