Is it worth the money to convert my Penn 50W (it's in very good condition) to a two speed? I'd also do blueprinting and bearings.

With the advent and use of spectra a wide reel here on the left coast is pretty much used for fishing the kite. I'm not sure where your located and if you use spectra, if not you may want to go that route. If you send it to a true reel guru like Cal to get the work done I'm sure you will like what they can do to it. Again a wide reel is a kite reel for me and do you want to drop that kind of money for a limited IMO use reel? All of the long range boats have kite setups that you can use so there is really no need to bring one unless you want to.

To make an effective decision, it helps to decide what line system will you be using.
Topshot length, possible stacking from 100 to 130, or from 130 to 200-pound braid, etc., etc.
Will it be primarily used as a troller, a kite reel, big live baits/chunks, or do you really need a sardine reel?
Do you have a strong sentimental attachment [belonged to father/grandfather]?
You can determine the "vintage" of Penn reels with the serial number; the first two numerals after the letter are the year it was built, so "A991234" was built in 1999.
Knowing the above will help your decision making and cost analysis.

I live in Florida and would use primarily for Swordfish. 100# class line W / Long topshot. It's an 82 model and works OK as is. I have the TRX 50W and will use the Penn as a backup.

I would only send to Cal

Froggy, For Fl swording, having it two speeded would be nice but you wouldn't need it sleeved and blueprinted like they do on the west coast.
They do this to the reels so a sardine can swim with heavy line. Our swordfishing reels do not need the freespool that is required for LongRange type tuna fishing. The stock drag on the Penn 50 IMO is fine also, especially for night time swording.

If I'm gonna send it might as well get the bells n whistles. Seems getting new drag and bearings is good maintenance. I am sentimental, I love all my children.

And if you foul hook a big one any extra pressure is appreciated. They do have trouble finding the hook with their mouth.

On a 30-year old reel like yours, new bearings are a good idea, as is the updated "Dura-Drag" material.
2-speeding is a nice touch, especially if you do foul-hook a swordy.
The "ultra-freespool" mods that Cal does will not be necessary for your application, but do be sure to tell him what specific drag range you want the reel to cover.
Sounds like it is not a "50TW", so one other thing to seriously consider would be a 1-piece frame, because the multi-piece frames of the day were not designed for use with 100-pound lines.

Thank you all for the advise. Replacing the frame, conversion, drag and bearings, I can save money buying a Makaria. I bought a Cavalla on sale and was impressed. Well respected people are saying good things about Okuma, never expected that.

Yes, when trying to update a 30-year old reel, the top motivation is almost always keeping a nostalgic connection [or your favorite "lucky" reel] going, and rarely a money-saving issue.

Kudos to Steve C in his advice.

IMO you have a family heirloom that brings memories to mind.

No need to do anything by cherish those memories and save your $$$ by going to today's marketplace for new gear.

I am an old east coast fisherman who has converted Penn reels over to 2 spd for LR West Coast fishing. The reels were used when I acquired them and no memories attached except those fish caught of Montauk Point.

We have such awesome equipment now available. make a choice based on your quarry sought... I like you am amazed by the quality of Okuma reels.

Thanks SDT; I should add, the new Penn models are among the most technologically up to date at any price, and current Penn models like the ones sold by Charkbait require no modifications to deliver high performance, although aftermarket work is a viable solution for those anglers who have older reels that they want to keep using for personal or other reasons.