Newbie

With your lack of schedule and budget I'd recommend a trawler, about 40'-50', maybe even smaller. There's some nice ones around 36'. It should give you the room you need although the king bed might become a queen unless you want to make some alterations. You'll need a davit to get the bike on and off and it'll eat up some cockpit space but it's manageable. Just keep it well covered and coated with CRC or you'll have a rustcycle. You might find it more practical to carry a pair of folding bicycles instead and then rent a car or bike where you want to tour farther from the marinas. Enterprise will pick you up almost anywhere. It'll also enable you to use a smaller davit or none at all and save you about $10,000 and a bunch of cockpit space.
I like that you're keeping resale value in mind. Too many don't. Most trawlers will hold their value pretty well, and many will fit your budget. They're also easily managed and handled by a couple.
Btw, upper and lower helm stations is a really good option for that trip.
Something like this could work well.https://www.**************/boats/1983/grand-banks-49-classic-3601540/

5' draft limit is for the Trent Severen which isn't necessary for the entire loop. I did it with a 5'6 draft with no issues. I'd stay under 65', you're also going to need to be under 19'2 air draft for the loop (illinois waterway). A catamaran will meet all of your needs without getting too long, perhaps something like a Lagoon 43/44' or a Leapord and in/near your price range. Another option would be an old hatteras 53' or smaller.

I'm not at all familiar with the Vic Franck. I think it's important to stick with a quality build, especially with older boats. Some use a lot of balsa coring that absorbs moisture and rots under the fiberglass. You mentioned windows. Be aware that, again especially on older boats, that's a place where leaks develop and they can be maddening to try to stop. There and around the deck. The GB is a make everyone knows and respects. However that king bed could be a stickler. It could be done by moving the cabinet under the aft hatch, but you'd have to design a work-around to keep the engine room hatch accessible. I think the king bed might be your biggest stumbling block in choosing a boat. If it's any help, after 43 years the wife and I still manage to fit nicely in a queen (I'm 6', 190) and the linens are a lot cheaper. The only place I see 5' draft being any issue is in the Carolinas or if you leave the channel. You'll rarely find channels along the loop that aren't designed to be at leas 6' deep and generally 9'+, but shoaling happens that can change that. Another point for boats like the GB is that they have a full keel. So if you run aground it's usually just a matter of waiting for the tide to come in or getting a tow off. Your running gear is well protected.

The draft problem on the loop is the Lake Michigan and South part (Tenn Tomm, Tomm Bigbee etc.) where getting into marina's for fuel and dockage can be a big problem.

Is there such a thing as a cat with a king bed? I'll 2nd the old Hat although the electric can be an issue with 2 x 50 amp and 32v DC. We did it on a 56' FBMY. The master was a queen, but there's room to expand it. Just a shame to hurt that woodworking.

Yes, the 43'/44' lagoon has a king sized bed in the master.

EEGELAND:
Power Cats are more stable and more fuel efficient at slower speeds. Most are very good sea boats. Very stable at rest. More room for their length. Dockage is always based on length, BUT finding slips for a CAT in some areas can be tougher. More deck/outdoor space. The 43' lagoon with large engines will cruise at 16.5 knots at 1.5 Gallons Per Nautical Mile, HOWEVER at 12 knots gets 2 nautical miles per gallon, and at 10 knots 3 nautical miles per gallon. So if you don't push her at cruise, she gets excellent fuel economy. Has great range also holding 400 gallons of fuel.

Cons- foward staterooms can be narrow. decent amount of steps to staterooms, finding dockage in some areas.

The problem are your requirements (like king sized bed) and your price range to find a good motoryacht.

Catermaran Pro: stable ride, large salon, shallow draft. Con: small staterooms in the sponsons, hard/ expensive to find dockage for due to their wide beam, (2) small engine rooms.
The old Hats are legendary, but they're getting old. Electric is an issue. As I mentioned on Valhalla we had to run out 2 x 50 amp cords and the DC is 32v which is difficult to find bulbs for. May be more space than you need.

In short...