I suggest you post your question over on the main Chesapeake board. You will get a LOT of responses there I am sure. The tackle board just doesn't get the traffic.
My recommendation for a reel is a used Penn 320GTi (used gets you the older ones...the quality has gone down since they moved manufacturing to China). You can get them on EBay or at the winter fishing flea markets for ~$50 (including shipping). As you said, Penn reels are bombproof, and can last forever with simple maintenance and easy to get parts. There are lots of local guys (including most of the tackle shops) that will do the maintenance for ~$20 or less, but you can really do it yourself (there are outstanding step-by-step directions with incredible photos by Alan Tani online at Fishing Reel Repair by Alan Tani - Index
A lot of Bay fishermen use the 330GTi...just the bigger version of the 320GTi. If you are only going to do light trolling (say to 8 oz total weight on your lines) the 320 is all you will need, but many folks like the 330 for when they do spring and late fall trolling with 20 or 30 oz total weight).
An alternative to the Penn 320GTi you might want to consider is the Okuma Titus T15L. Its about the same weight as the 320GTi. The lower Okuma line of reels can be total ****, but the Titus line is very popular with many good Bay fishermen I know. Recommending Okuma is hard for me to say (as a dedicated Penn lover), but I do have a T20L (in the 330GTi class), and I must say its a mighty smooth reel. You can get a new T15L for ~ $90 retail.
For rods: don't go too heavy...you really don't want a broom stick rod for the type of fishing you are talking about. A Medium weight is about perfect: a MH is absolutely as heavy as you want to go. I would look for 6'6" M rods. (6' would be fine, but 6'6" is much more common in less expensive rods).
There are a lot of real **** rods out there; they are sold as nearly give-aways, with the vendors knowing you will be back in a season or two after the eyelets pop out. Penn Slammer rods are an infamous example of this. Penn makes some perfectly good rods...but the slammer isn't one of them. You often find them bundled with Penn reels, and by comparing prices you realize they are giving the Slammer rod away for free in the combo...worth every penny of $0.
Shakespeare Ugly Sticks, Berkely Lightening rods and Penn Mariner's are all perfectly good, durable rods you can get for <$50. Lots of sales on rods exist at various times, so its pretty easy to beat that price if you are at the right time and place.
One place you might want to check out is Tylers in Ches. Beach. They have a winter sale next weekend (1/17-18) and you can probably get some great deals. Guaranteed you will get the best advice available there.