In particular, I know gmail hold IPv6 to higher standards. Some things (e.g. rDNS) that we traditionally treat as 'should', gmail will treat as 'must' over IPv6 - it's being treated as a chance to drop a lot of legacy leeway.
I do run my own MTA. It's not high-maintenance, at all. Understand the pitfalls, iron them out, and then stick with it to build your reputation. There is no magic bullet - the big providers won't tell us how they measure us - the best we can do is be well-behaved, stay well-behaved, and adopt modern standards (TLS, SPF, DKIM, etc) as they're thrown at us.
My best advice is to choose a reputable host. There's a lot of race-to-the-bottom in the web hosting market, and VPS are turning out no different. Keeping a clean house is good for your reputation - but so is living in a nice neighbourhood. It's well worth a couple of bucks extra to find such a neighbourhood.