Firstly... how long are your arms? 5' is a bit wide for SFG. Sure, it can be done, but the idea is to not step in the bed. I use 4' and I have long arms. I guess I could do 5', but it would get old fast. Try it the first year and see how it works out.

Next, I think I would put the squash up front (southward). You could let it cascade forward (again, towards the south) into the walkway. A bit of a pain, but a good way to maximize growing space.

Next, the eggplant. Yes, stake or cage them, but they only get about 4'. or so tall. Those cheap cages work good, but any stake would do just fine. If nothing else, cages and stakes help the plants grow upward and stay neatly in place... an important factor in crowded spaces.

You seem to be missing labels for the cherries. Are you doing 4 and leaving empty spaces? Also, you have Moneymaker listed twice. I looked them up, and 1 source said the vines get about 5' tall. At least one of your cherries get over 6'. Most SF Gardeners like determinates. This doesn't preclude indeterminates, but put your shorter varieties toward the front. Be prepared to prune if necessary. You could stake the maters, but look into a weave. Just takes 2 strong stakes on the ends of each tomato row with twine running across. It's a good space saver, but you may need help to weave it as they grow.

Finally, make sure you do a trellis on the back for your cukes. Properly trained, they won't need a ton of space. A metal fencing, or concrete reinforcing wire supported on the back corners of the bed work very well, are durable and reusable, and since you won't need much, won't be too expensive.

I may be missing things, but those are my first impressions.

This is great! And yes, 5' is not ideal, but the community garden I am renting from doesn't have any 4' wide beds. The smallest available are 5'x6' and so I got slightly longer but, sadly, still just as wide. I could just completely eliminate the middle square and just do the 2' on the outside, but I tried to make due as best I could. That's why I left those two middle squares blank.

Great idea about moving the squash to the "front" south side of the bed, I'll re-org that tonight. As for the 'maters, I figured that I would just prune and top them off as needed, but would either do a twine support like you mentioned or possibly cages for all of them.

So from north to south, I'll have the cukes (trellised), tomatoes, then eggplant, and then the squash trailing over the south side.

Thank you for all your help!

Maybe something a bit more like this? Would you recommend doing 1 or 2 squares per cherry tomato? Here I am giving two squares per plant. I left the "5th" middle row empty to keep from having untenable growth there. As far as the squash "row" I think I'd plant 3 plants there, maybe 4?

Hopefully more people will comment, but look up the expected heights of those maters. If the Moneymakers are only 5' tall as 1 source said, they will top out in height without pruning being necessary. Put the shorter varieties toward the front. Look up each variety from multiple sources and take the average.

I do think you will indeed be happier doing a 4' wide bed. If I may make another suggestion, true, leaving the space down the middle will alleviate crowding, but also consider leaving the 1' blank space at an edge and just step on the bed, or run a plank from front to back. I agree though, that it's not needed for the squash area. You can reach those from the front and the sides. My reasoning is that with a 4' bed you can reach the middle from both sides. If you leave the empty space down the center, anything in there will be unreachable. I would push everything behind the squash together, and leave the 1' blank space on either the east or the west side, whichever is more appropriate. Run a plank down that blank space to step on when reaching in... voila... 4' wide with plenty of root space under the plank. But again, this will depend on whichever choice is comfortable for you.

You could just put a few stepping stones in strategic places and step on those to harvest plants that you can't reach.