It is worth noting that the continuous rating of the connectors is much higher than the number in the name would imply.
Running a high power winch for more than a few minutes would normally mean going with a connector that can handle the load at its continuous rating.
So, unless voltage drop is a serious consideration, using a anderson connector at higher than its rating for brief periods is okay. For example, jump starting a car. I have a Anderson connector in my engine compartment for using a front winch. If I use it for jump starting a vehicle, it could see 500A for a second or two. This doesn't mean I need a 500A rating connector. The ~200A version is perfectly fine.
Anderson connectors are self wiping, so they don't need much maintenance. A rain/dust boot is preferred. You need to use adhesive lined heat shrink over the connector though. Water penetration into the wire or the back of the connector will cause corrosion in short order.
A bit of dielectric grease on the connectors from time to time is good maintenance. Also, unplugging/replugging a couple times a month will help keep the contacts clean.