Roaming, second-guessing Blues

I had a frustrating night roaming with a friend, and I blame myself for it.  Perhaps I wasn't in an aggressive enough mood or something.  We were walking through lowsec in the area around Dantumi, since I had bookmarks, clone, and ship there from the Deathrace aftermath.  He got into a Hawk while I was flying my Thorax.  Warning: These are random thoughts more disconnected than my usual posts.

What are the keys to roaming and finding fights?  Should we bother trying to scan belts and such or just recognize that anyone our size will bug out when they see us hit local.  If so, should we be trying to spent the minimum amount of time possible in each system?  We were leading with his Hawk (with me staying one gate back) for a while but once we spotted heavier opposition I moved into his system out of fear that he could be tackled and burned down before I could arrive.

Or is a cloaky tackler what we need?  It won't solve the local problem, but maybe...

Chased a Cormorant out of a FW Medium, but then didn't try to engage when it looked like he had pulled three other FW buddies into the mix (judging from D-scan).  I think it was Cormorant, Comet, Merlin, some interceptor I can't remember and a Hookbill.  The Merlin was named "Jakob's Merlin" when we d-scanned it - was that coincidence, an attempt to mislead a third party, or an attempt to goad me into action?

Spent some time bumming around a system figuring out D-scan while we noticed capsuleers belonging to Pandemic Legion and some (local) corp slowly increase in numbers.  I haven't been hot-dropped roaming before - maybe we should have found some way to engage PL instead of running off just to see if I could check that off my list. :)

Got too rattled when a -10 capsuleer came into system, shortly followed by another -10 from the same corp.  Sure they could choose the fight and would be more experienced, but at least it would be a fight.  I wonder if the Cynabal in the POS we noticed was theirs...

I never saw a combat probe on d-scan the entire night.  Perhaps in this area of lowsec pirates are more used to engaging on celestials?  Or did no one really have any interest in jumping us?  Or did I screw up my overview somewhere?

I've been reading too many wormhole blogs.  A guy jumped through the gate I was perching above, right into my buddy on the other side, and then turned around and crashed back through the gate to avoid him.  My brain said "quick he's polarized".  Doh, no.  Wrong system.  Anyway he was able to warp off faster than I could scram him.  Should I have had a Sebo to do roaming?  Can I afford to lose that slot when there are only two of us?

Is roaming as a duo feasible at our level of PVP experience (i.e. not much)?

I suppose the bottom line is I need to get out of our little RL-friends corp and into a bigger one where I can learn more.  Now that I've gotten some decent cross-race ship and shield skills I feel like I'm more able to contribute.