Early 1950's. The reel is chrome plated and the box is Penn. I recently sold one from the 1940's and it came in a LL Bean box with a nickel plated reel inside.
I sold my L L Bean model in the L L Bean box privately for $50.00 to someone I know, maybe on EBay it would have went for more, the buyer did not hesitate at $50. The 249 is not a high end Penn reel. Mint ones sell for about $25 or $30, mint in the box would bring it higher and beat up ones are candidates for a reel tossing contest. I would guess that your reel would bring somewhere between $50 and $100 on EBay but that is just a guess, maybe more or maybe less. It is hard to say because it is a Trade Reel and trade reels break the rules sometimes.
Horton Mfg. Co. also made a lot of trade reels for L.L. Bean, including the Bristol 77 bait caster, the Bristol 65 fly reel, and the Bristol 69 spinning reel. In terms of value, the reels and reel boxes are pretty much on par with the corresponding Horton models. I would imagine the same thing would be true of Penn trade reels.
I have had a few 249's and have one left in a 1950's box. I have never seen one in a velvet bag or any other kind of bag for that matter. I suspect that was added by a owner.
I would agree with you about trade reels but I think there is a growing interest in them concerning Penn and Ocean City. Especially trade reels that can be tied to a large company like LL Bean, Tryon or Sears. For the most part, Penn and Ocean City trade reels have brought less money that their standard production sisters, case in point is the Kingfisher in a box that just sold on EBay for $66. The reel was a 1933 Sea Ford. If that reel had been a regular production Penn 1933 Sea Ford in the original box it would have brought $150 or more, IMHO.
Anyways, all of this is only how each of us feels about a market that is very interesting but fickle. Values go up and down concerning all reels and trying to put a reason to it is always speculation at best.
I want to make a different speculation on the date of your 249. The 249 was introduced in 1939, since that reel is a trade reel the plating and handle may be different than a standard production Penn. The box with the Model Name of the reel printed on a slant like that one is may very likely be a pre-WW II box. I believe your 249 is from the early 1940's.
To my knowledge, Penn catalogs were not published in 1942, 43 and 44. I do not believe they were heavily involved in war products production but they were definitely not making reels in any production numbers. When I refer to early 1940's production, I mean to exclude those years.
I have seen some of Penn's advertising from during those years, Penn was very busy selling lubricants and giving advice of how to care for reels and make them last through those hard times. Luckily, production of Penn reels was heavy in the years before the war and product was available on tackle shop shelves throughout that period.