Pressable includes support, global caching, and a bunch of other things you won't get on a $5/month VPS. Also not everyone wants to play system administrator 7 days a week to keep their server from getting hijacked or nuked.
Of course, it doesn't matter in the end - as long as users have ability to choose a hosting there will be cheaper and "better" options. Shopyfing wordpress would be worse...
Just find a good indy shop. there's a great one 2 blocks from my house at a gas station. discusses all repairs with you, good on preventive maintenance, 1/4 the price of a dealer. Will tell you what repairs you actually need to do and what you don't. Also easier to schedule and pick up and drop off. I have to wait at the mega dealer near me like 15-30 minutes at drop off and pick up. At least the toyota one will let you defer your car wash instead of waiting for it longer. At the gas station I drop the car in the lot and drop the keys in a mailbox. For pickup I go in any day till 10 and pay like I'm buying an energy drink, grab the keys and walk out to the lot to grab it.