Creating a sitemap - Software / Best Approach

Hey all,

This is my first post as a registered user though I have been skulking on the forums for over a year now.  You all are awesome and the wealth of information in here is staggering sometimes.    

So, we are on the journey of building up our homestead of 23.3 acres.  I would like to share the dream / vision with you all.  Before I do that - I have a simple question that I would love advice on.  

Can you offer advice on the best software / methodology / etc. on building your homestead sitemap?  I really want to build something robust to allow for us to plan the site in terms of areas of development.  Also, I want to be able to layer in that information as we go to show everything from succession planning, field rotations, etc.  I tend to be a very visual person and I feel like this would be an enormous tool for us to use.

Looking online, I see a ton of option (many suggested here on permies).  Online tools / CAD-like software like SketchUp have some benefits.  Also, I am rather adept at Photoshop - which could make the layering process much simpler.  I really, really want to make something that looks like this
.  This image is sourced from https://www.overhillgardens.com/landscaping.html (not advertising, just attributing).  

Right now, the plan is to do the following:

1.  Using Google maps, get a working image / scale of our site that I can use to begin to overlay information.
2.  Using geopositioning, start to work out landmarks / information for the base sitemap.  (Cellphones can be accurate up to 10 feet)  
3.  Find a good asset library to import
4.  Combine all elements using Photoshope.

Anyway, anyone have suggestions on best process for creating a living sitemap?  Are there great asset libraries to tap into or ways best processes to use?  Am I going overboard here?!?!

Sorry to pour water on a great idea; BUT I feel I need to.

I have used computers since about 1967, have written software and seen the growth and use of computers and software.
Its a unique situation to be in.

I believe if you cannot draft something on paper initially no amount of software will help.
Nothing beats the speed and ability to change the design than pen and paper!
I think you need the concept in your head to transfer it to paper and or software, and many cannot do that.
I dont know if its a learned or innate skill but it helps.

Only then is it best to use some software to set it down so it can be enhanced and printed.
Software can make a simple task complex, be careful of that fact.

I might be able to get behind both concepts above:

1. draw/draft something up by hand

2. get the results into a (free) program that does layers

Go back and forth between the two until the layers make sense. Beat the crap out of it until it is both homesteading + permaculture.

That last little part is mine, as I attempt to uncover PDC's (syllabi), educational materials within (what each version of the original PDC offers today's students), and finally, learn enough from it to apply the concepts of PermaCulture.

For item #1, I agree that the software tends to get in the way of the initial design process ...
 - having been an architectural draftsman (pencil/paper & drafting table) for many firms in my earlier career, nothing beats just getting it done quickly on paper ... after an architect hands me the design sketch, and says "make it so". If I'm doing the design, then out comes the butter paper (roll of sketch paper), and lots of iterations later, there is a design, which then can be drafted, with each relevant page being a layer. While that was all a long time ago, I still today reach for my "drafting table", which fits in my lap, when I need to design/draw something (usually on the couch, early before anyone else awakens). The attachment shows such a board, roughly 12"x18" ... available on Amazon and other venues. I can draft on it, or sketch on it with the butter paper.
 - if I try the same thing directly in a CAD program, the interface gets in the way of me designing, while I try to find the command that my mind envisions. I've tried sketch programs, which work a little bit, but I personally need a big touch-screen and other tools to input the design stuff. A little laptop or tablet and my fingertip, and things look more like a seismograph reading than a sketch. So, it's back to paper for me ...
 - if design sketches or drawings needs to be saved digitally, it is captured on the phone, and sent wherever. If really necessary, I'd blow it up to scale, and make it a layer in some CAD program.

For item #2, there are so many free and open source software packages to choose from ... no money should need to be spent. I'm thinking tools like:
 - LibreCad: if the need is cad software with layering features (but there's also SketchUp [ 2017 free version ], qcad, draftsight, sweethome3d ... whatever free tool fits the need). In any product, the layers are built upon my initial paper sketches, or google earth stuff.
 - QGIS: if the need is GIS
 - Google Earth (pro version, which is free)
 - fonts: I still letter by hand, so I'd print a drawing, and hand letter it to get that architectural (I call it my "draftsman" font, but ...) However, there are quite a few free architectural fonts, like Flux, TK-Architect and many others; just get the .ttf, right-click and install it, and you are now lettering like I do on paper.

Google Earth and such have already drawn (photo'd and map'd) our 40 acres for us, and it shouldn't be hard to extract GIS-like info in different layers from Google Earth, to become the starting layers (topo, existing trees/vegetation) in the cad program (or OP's photoshop, as the lines blur between CAD and IMAGE software).

With the drawings done (as-built, roads, trees, and such, in various layers), it's time to apply the can of PermaCulture spray-paint to get the final layer ... no spray-paint? No permaculture crayons? Hmm ... back to the "drafting" board ...

I have never seen that style of drafting board, but `i can see it would be handy at times.
I have looked at software and just find them missing something.
I am not sure what is missing, but they dont seem to be straightforward in the manner they work.