i beg to differ.
see post #8.

ps:
ok, getting philosophical - clearly this depends on your definition of flawless and, ultimately, on your expectations.

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And efforts, a lot of the light weight DEs or WMs use code for that.

Now that we know what you did to come to the conclusion that you were satisfied to call it Solved you could do that.

I am pretty busy now so have little time to mess with this. I am sure there is a workable solution.

I am pretty much a OB noob. One thing I really need to do is spend some serious time on the OB site. And links from it to user scripts and ideas. OB has been around a good while. The *boxes have a long history and many very clever users.

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some of the stuff on openbox.org is badly outdated.
but the mailing list is very active and noob friendly.

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I might have misread your question, but why don't you just use the Debian's "menu" package?
https://packages.debian.org/jessie/menu

An other (and more OB specific) option would be "openbox-menu" (from the LXDE team).
https://packages.debian.org/jessie/openbox-menu

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It seems Salix OS(Slackware based) have OB working with dynamic menus. I'm not sure how they have it doing it. They offer an Openbox iso and it's setup using Lxpanel.

Thank you for that information.

I will grab an ISO for that and give it a whirl.

I definitely will not be using the lxpanel on my OB installs but worth looking at to see how they deal with the menu. I suspect, haven't had time to check the package out yet, that they are using the lxde menu too which does work very well.

When I was exploring different DEs I tried Lxde and OB at the same time on separate installs. Decided I was more compatible with OB. Found myself actually using OB native tools for things in Lxde and when I caught my self selecting the OB session in the Lxde install I dropped Lxde.

That is not in anyway a put down of Lxde. Just doesn't fit with me. So just assume that this is a personal problem with me. I most certainly can see that it is a much better choice for a noob to the world of *boxes if they don't feel like really messing with it.

I have now gotten to the point that I want the menu to work dynamically. I don't have small installs. I use a lot of applications and editing the menu is time consuming.

Obmenu works for doing that job. I find it much slower for me than direct editing. Opening things in cli works but if you use a lot of applications at once you end up with either a lot of terminal windows open or, in my case, a lot of tabs open in a dedicated terminal window for opening all applications wanted.

I generally have 8 workstations and most of the time they are all populated with at least one application and some with up to three applications.

But I have tint2 set up with a few launchers for very common applications, and segmented for each of the workstations.

WS7 is dedicated to $ terminal(s), WK 8 to # terminal(s). I use the xfce4-terminal so as to have easy configuration and tabs.

WK 1 is for web browsers, WK 2 is for Thunar or some other file manager, WK 3 for an Email client usually Icedove or Claws.

The rest are for all the other stuff that I am running at any point in time.

After the menu is straightened out to my satisfaction I need to come to grips with OB key bindings. Once those two things are in place it will be a regularly used environment instead of one that I use only sometimes mostly for fun edification.

Note the second link I posted above (https://packages.debian.org/jessie/openbox-menu).
You can add an "applications" entry in the default OB menu using openbox-menu (or/and "menu" if you prefer to display everything on your system).

You know, I saw openbox-menu and assumed obmenu. What a moron.

Looks very interesting. Does use some of the Lxde stuff that seems to work well.

Exerpt from apt-cache show;
Will have to play with that.