layman tangled in 6to7 major upgrade

I seem to have become entangled in trying to do a major version upgrade (on a bit of a Frankenstein project to boot), and wondered if anyone could set me on a better path.

My backup is done, I thought my mess of contributed modules was all spiffy and up to date, and I am running the lasted version of 6, so I thought I would be in a good place to try the drush site-upgrade command (referred to as magic in some posts ) but while I get to Stage 1 of the status report I seem deeply stuck there. The list of possible issues is LONG, so I don’t want to jam up a poor generous soul willing to read/chat/respond with them all but (BUT….) prioritizing them is a little beyond me, I think.

Possible big picture show stoppers include: I have read site-upgrade is not good for remote set ups, and not all drush commands work w Windows (though I think I downloaded the sup stuff and charged on w blind hope anyway). So maybe I’m dead in the race before the gun.

Some details:
Running D6.27 on a hosted development space (which I have fallen fast in love with) optimized for Drupal running Drush (5.1)
Local Windows 7 64-bit environment. I am new to Git (1.8.0-preview20121022) and Drush (5.8). Local repository is not in a www space, but wamp is installed just not being used (trying not to pile on learning multisite stuff on top of all the other stuff that’s new for me and was earlier on in my pre-drush dreams trying to just have a static code repository and keep it all breathing on the hosted server).

I am not quite sure how to read/interpret/respond to the status report. I don’t seem to be doing the UUID patch correctly, and can’t for the life of me understand the path_alias_cache and git_deploy suggestions, both of which I thought I addressed by installing more! modules but no matter how many times (please don’t ask for the number ) I run the report, the suggestions still show up. Content taxonomy, features, and token are also mentioned in the notes, but I keep pushing them down the list of concerns, though it suggests I wasn’t as well prepared as I had imagined.

O, and I tried to write a new group alias file for the new site specs, and that went wonky too I bet.

Considering regrouping to an FTP process, but I have several taxonomies (nested terms) and CCK content types/fields (multi values, images) that might get a little hairy, so I’m concerned. Considering also a build out in 7 and pulling in what I can (least favorite option).

Any and all guidance most welcome! What I am looking for mostly is help in prioritizing the likeliest showstopper, or pointing out the one I obviously missed or misjudged. I feel so close yet so far. Thanks for reading!