I have probably put more thought into this than anyone should, but the ad is still in the launcher, so here we go.
Stain seem to have two good looking places to connect low-sec with: G-ME2K (-0.3) that is currently a dead end, and a small group of F7-ICZ (-0.3), T-NNJZ (-0.3) and NRT4-U (-0.3). Both locations are choke points, that gankers could easily take advantage of.
As for the other end, there is Tash-Murkon: Saminer (0.3), Domain: Misaba (0.1) also connected to Providence, and Khanid: Moro (0.5), or if low-sec is necessary Efa (0.4) that is connected to Querious.
And in the middle of this group of systems, there is also Catch: 4-07MU (-1.0) that could also be used as a direct connection to Stain and/or low-sec.