Welcome to the club, Lenny.
This is a local problem which is under intense scrutiny at the moment. It is unlikely that Amtrak will be involved in any way with this problem(unless later contracted), and more likely that the state of MD will be completely involved. This fact is not lost to the state of MD. The summer population of OC, MD has remained relatively steady, while the summer population of the DE beaches has expanded considerably. The state of MD is not happy about building a new bridge so people can go vacation in DE!
NS does operate the north-south oriented line from wilmington DE , down to the former eastern shore railroad interchange in pocomoke. As the fledgeling regional transit authority (shore transit) begins to develop, they would be fools to not dream into the future about DMU service along the current line from pocomoke to wilmington. (Condition wise, ESR is in poor condition, and the NS line appears to be in good condition, not sure what would be required upgrades for passenegr service... must be slow limits, thought...) This is no where near reality today. But north-south traffic is not the real problem.
In the summer, Delmarva is overrun by touists from west of the Chesapeake bay. It is this east-west traffic that is the problem. The William P. Lane (US 50-301) bridge is already operating over it's capacity in the summer. There is an ongoing study to determine how to solve this problem. The current crossing approaches can not support additional lanes on the bridge, and NIMBY is preventing any of the other bridges from being seriously considered.
Public transit of some sort is the piece of this puzzle that has been strangely IGNORED. NO form of transit (bus, rail, ferry, ect) has even been considered.
(Ok, fast ferry was in a seperate study, but discarded. Ferry service is close to possible)...
When a vehicle crosses the US 50 bridge eastbound, there is a high likelyhood that it is headed to the beach (especially in summer). It is in these narrow pipelines that public transit can be very effective in.
In my dream, two stub trains begin their eastward journey... One starts up in Baltimore/hartford county, and the other starts south of DC. Both stubs meet and combine somewhere along the way to Annapolis, where they then head towards and under the chesapeake bay (It HAS to be a tunnel, and it's going to be deep and expensive, but I don't know where a ROW could be created).
The tunnel can emerge on the western side of the bay in the old ferry terminal. Once on the eastern shore, there are two routing possibilities I see, both terminate in Ocean City, MD.
The first travels east (new ROW?) towards harrington, DE (connect to the slots at harrington.... a tourist attraction), then follows south along the NS ROW into Salisbury, MD, and lastly follows the abandonded (but intact) ROW east into OC, MD.
The second follows route 50 through easton, cambridge, and into salisbury. This route would require many more bridges, and has significantly more engineering problems. But, this local route would serve the MD taxpayers much better. I'm not 100% sure this old ROW is still intact.
Most tourists don't need a car in the ocean resorts. They should be able to leave them on the western shore, and I believe this is a viable (but expensive) plan to do just that.