I had to rework my plans after a discussion with Elite (Rock's summon counts as a traveler, apparently its a no-no to ditch people in the wilderness to pick up more favorable NPCs, Sandru is a driver and never a guard), which is why this wasn't posted earlier.
For convenience, this is the list of jobs that I understand our group to be capable of. I use 'Monkey' for Rockem's mount 'cause I don't know its name. Sorry, but I don't really get your character sheet.Job List Travelers
The above is the setup I recommend. Everything else in this post is just expository. I use "Hunter" to refer to scouts that gather food and "Outrider" for scouts that provide security, except there aren't any outriders, ever. That's because there's a max on scouts but not on guides (who are cheaper to hire), which do the same thing as outriders (they're pointless). If you ever do see "Scout," it is of the hunter variety. A few (preferably all) of us should put skill ranks into wainwright so we can repair faster without hiring waste-of-space wainwrights (they do nothing most of the trip).
In terms of feat/stat selection for our caravan, I highly favor the defensive options. Our caravan consists of our supplies and important NPCs, any form of loss could be highly detrimental. Unless there are foes only our caravan can damage, we will quickly outpace (as in have already outpaced) its paltry d6+level damage (which takes significant investment in feats requiring X offense to pump. Even by then the caravan offensives will really lag behind individual party members, at the expense of all else). If we for some reason find some mega wagon-mounted cannon, the caravan can probably still put out a decent attack by just converting some travelers to guards (the feats aren't that strong).Feats/Stats picks
Regarding the starting feat, Lucky Caravan and Extra Wagons seemed the strongest. Circle the Wagons also looked good, but it probably should be passed up until later while our caravan's attacks still hurt things. It would also require a defense of 3, delaying acquiring Extra Wagons. I opted for the reroll since 2000gd just can't handle purchases of 3-4 wagons. I made sure starting mobility was 3, however, so that we can pick it up as soon as it becomes feasible with our funding. I put the other stat increase in defense so we can start heading towards Circle the Wagons (caravan AC is by far the hardest thing to increase) and Caravan Toughness. The morale feats aren't really up to par, and only really help once we've maxed out our base caravan statistics/travelers bonuses.Discarded Setups
My first build, edited a few times as I understood rules better. It has worse stats than the other builds, but is 4 wagons (put the 3rd stat point into defense rather than mobility since we can delay extra wagons longer) and leaves a nice amount of extra money.carv
A modification of the above, the idea of this build was to improve stats via hirelings/less hunters and use a supply wagon full of stores to compensate. That didn't work so well, but it ended up having comparable stats to the recommend build with more money left over.1each
An attempt at a "bare bones" 4 wagon build where there were no hirelings. To properly do this, Rock would have to unsummon his friend while the caravan was moving. The result is worse stats and no extra traveler capacity for NPCs on the road. Barf build.nohires
EDIT:: now that I think of it I mistakenly included Totino in the party count. Just mentally move him to hirelings and move the "hero" job from him to Elliot. At 1/5 the encounter treasure, he is burdensomely expensive. Optimally we'll trade him out as soon as we max out on spellcasters.