I've worked in companies with horrendous security, where someone with just a bit of SQL injection experience could have easily carried out the data. Yet, since this was a custom in-house application and your off-the-shelve-scanners did not work, this never happened; the only times the servers were hacked was when the company decided to host an (obviously never updated) grandfathered Joomla instance for a customer.
But even more simply, just setting your SSH port to something >10000 is enough to get away with a very mediocre password. It's mostly really not about being a hard target, not being the easiest one is likely quite sufficient :)