Crazy or Jackson? I can't decide >_<

[Reserector]

You are right.  It has been slow around here.  I'm always around, though.  Welcome to the site.  

I've been inactive as a skater for a few years, now, so I am not familiar with either of those boots.  But I will say that a close-fitting boot is probably most important.  Not too tight, but you don't want your foot to move around in it, either.  
As for plates, I would only recommend plastic if you are fairly light.  Say around 175 or less.  Tis depends on the quality of the plate, and the size of the plate.  Shorter plates will flex less than longer plates.  The concern is flex that can strain your arches.  If the plates can flex, they will also affect turning, and CAN feel wobbly.
There are some really good plastic plates, but "good" comes at a price.  Maybe not something you want to risk beating up outdoors.

I'm a big 'ol boy, so I use aluminum plates outdoors.  They don't feel like they are weighing me down; they feel very solid and predictable to me.

For wheels, favor wheels that are tall, narrow, and in the 70s on the durometer scale.  Tall (large diameter) wheels roll over pebbles and twigs better, but you will be limited by what the plate will clear.  Most plates will handle up to 65mm diameter.
Narrow works well because they run into fewer pebbles simply because they are narrow.
Soft works because it absorbs the rough surface, causing less vibration.  Vibration equals drag.  Soft wheels roll more easily outdoors than hard wheels.  Totally opposite from a rink floor.  I would look at "aerobic" wheels, and Sonic wheels for their characteristics, and search for wheels with those characteristics, or just go with those.  

As for bearings, the cheap ABEC3 and ABEC5 seem hold up the best.  It seems like the ABEC 3 are more forgiving of a little dust getting in them.  I've run all sorts of bearings outdoors, and ended up using the cheap bearings.

By the way, when was "back in the day" for you?