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Hi! This is one of those software requests where I've got an idea what I want, but not completely able to specify it start-to-end. If it seems hazy, please ask clarifying questions, or suggest your own experience, and pros+cons - thanks!

So, I want a vector graphics package that handles scaling in a more helpful/intuitive-to-me way, than most seem to. I'm mainly on Windows, so anything that's Win7 - 10 compatible is probably fine. I'm equally okay with free or paid: design/usage quality and "do I like using it" is more important.

I use Photoshop, and I've used Visio and EDraw Max. I haven't used Illustrator, Sketchup Pro, Inkscape or most other sketch programs, and I don't have any CAD experience to work with but most CAD can handle 2D as well as 3D.

If the software has extra features/rich feature set, there's a chance I will end up using them, so that's fine. I don't mind if it's "overkill" so long as it'll do what I need smoothly and well. If it's intuitive, well thought out UI, and fairly mature/not many embarrassing bugs, that would be a very big "plus". I don't use much 3D, so 3D is worth having, but not the most essential thing. To be honest I'm not sure what I want in 3D yet, so I'm focusing on my 2D needs here. There are really just 2 of them:

General sketching (easy)

My first vector package was in the 1980s, using Macs - MacDraw. The ability to quickly draw objects, group them, and specify as properties, their sizes, angles, connectors, how corners should merge, and other parameters. A bit like how Microsoft Word or EDraw Max handles generic shapes. If I want to sketch something, I'd like a go-to sketch program that I can add this or that shape, and juggle them about until it's right.

Obviously these days any decent program will do a lot more - distortions, blends, handling raster images within a vector image (including smoothing/resizing/cropping them). But basically, a go-to sketch program.

I also need, for floor plan purposes, to be able to specify linear elements such as walls, that have a fixed thickness but vary in length. I assume that's easy in most programs though.

Scaled drawing approach (not so easy!)

This is the area I've had problems finding a decent software choice.

I do a lot of different kind of scaled drawings - engineering parts, floor plans, layouts of areas and spaces, and technical drawing.

This is the single most important "usage issue" for me.

Most sketch programs with scaling seem to obsess over the "drawing to display" scale factor, or "printed page" scale factor. I do not need or want to specify an actual on-screen or printed scale for my sketch (as in "1 pixel on screen = 10mm on plan" or "1mm on printout = 10mm plan"). I actually don't want the program to care about the display size.

I want a different approach.

All I want to give it is the "real" sizes of each element in the drawing, and a "canvas" (maximum working area) size. That is, instead of specifying a scale factor for my plan, I want to be able to say nothing beyond "this line is 1200mm long", or "this circle's centre is 400mm down from that corner", and I will sort out the display scale by simply zooming in or out when I'm working.

By that I mean, the onscreen size is a moment-by-moment viewing not a sketching choice. I tell the software what actual size an object is, and the display shows the drawn object(s) + a ruler. If the objects are too large or small as viewed, I'll zoom to a comfortable level, and the ruler will automatically change to reflect my current zoom.

This also goes for printing the plan. I want to specify the area to print (or all of it) and how many pages or what size to print it, and the program to autocalculate scaling so I get that printout (of course I could also specify a scale factor and region to print, and it'll print it on multiple pages if needed).

I need this approach because scaling is a real-world issue. In Visio and EDraw, I have to designate what scale I'm working at. As an extreme example, if you are dealing with a single sketch of a site plan, and at the largest scale your plan includes a whole 8 acre site, and at a smaller scale it includes detailing of a building access doorway, you need to create 2 diagrams with these.

With my preferred approach to scaling, I can have one drawing, which is sparse in some areas, dense in others, and if I just want a specific area, I zoom into that area or print that area. It doesn't get simpler.

If you have a building with an annex and you want some drawings with the annex (smaller scale) and some without it (larger scale), again it seems unnecessarily complex in many programs. You can't just pick a rectangular part of the plan and say "show me (or print) that rectangular region fitted to a single A4 page with a ruler".

All that a program should need is the "real world" or designated real size of each element, and their other properties; the scaling should then be as simple as zooming in or out on the screen, with a ruler that's updated to show your current working scale.

But I don't know which sketching programs work that way.

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Your question is a bit confusing because it seems like you wish to have features you find in a CAD application included in a Sketching software. So here I will recommend not a single application but a combination:


LibreCAD / Sketchup / AutoCAD

Now from what I have worked with, you can do what you wish in your "Scaled drawing approach" with AutoCAD or any other CAD application (I also suggest LibreCAD), in which you can just draw your projects in actual sizes (a 10m line is a 10m wall), where you would just need to do initial setup do establish your default scaling requirements and also your plot layout. Done your initial setup, your workflow will be seamless and easy. When you plot just select the scale you wish and the software will automatically adjust the plot to said scaling. For your purpose I believe a CAD application will solve ALL your needs, except for the requirement to be user-friendly-out-of-the-box. But once you get the hang of it, you will find that everything you want can be done with this application. Just keep in mind that LibreCAD only works 2D. For 3D alternatives to AutoCAD there is FreeCAD.

Sketchup is apparently also a great tool, however I have never used it. But from what I understand it is actually a package of 3 modules (Layout, Style Builder, Sketchup Pro), where you go from 2D, to 3D to texturing your models. It seems easier to use but again, I have never used it so am not sure how it would fulfill your requirements.


Inkscape / Illustrator

Now for your sketching, this is your known, Inkscape, CorelDRAW and any other application to draw vector graphics. Basically kind of like free-hand drawing and avoid seeing pixels. For this I would usually recommend Inkscape, mainly because it is cross-platform, so once you learn how to use it, it doesn't matter what operating system you change to in the future, you will know how to use your vector drawing software. The downside is that depending on what your line of work is, you may need to use Adobe Illustrator, mainly because a lot of the resources available online are in this format. But since it appears you work in the construction business then Inkscape would be a great solution for you.


Conclusion

So, considering what you want in the "not so easy" part of your question, I would suggest LibraCAD (AutoCAD if you don't have financial restraints), and use it along side a Sketching software, which I would recommend Inkscape. Both LibreCAD and Inkscape are cross-platform, which in my opinion is a very strong point to consider if your are selecting a software for your working needs.

http://librecad.org/
https://www.freecadweb.org/
https://inkscape.org/

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Sounds like you are describing classic CAD or BIM, and as your examples are all specific to site and architectural design, I feel like you should be looking at things like Draftisght, SketchUp, Revit, ArchiCAD, Bentley, Onshape, FreeCAD - or possibly Affinity Designer or Illustrator.

I'd start in your case with DraftSight, which is super effective CAD, freeware, and does do both 2D and 3D, but is optimised for 2D draughting.

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