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First of all, my apologies for my complete lack of ignorance of all things Linux. The last time I had a linux box I used with any regularity, President Clinton was still in office.

I am running Ubuntu from a 2 partitions 64GB USB3 thumbdrive (one for Ubuntu one for files).

I don't have a huge SSD drive (yet), and I need as much of the space on it as I can for my Windows 10 installation. Also, I would like to run the same instance of Ubuntu on my Laptop, desktop and my wife's laptop as needed, without having to reconfigure Ubuntu each time or have 3 separate installations.

I have done some tests already and I have read many relevant posts on this and other forums, however, I have encountered some issues:

Upon Installation (after running Ubuntu in "Demo" mode off the USB TD) I was unable to install Ubuntu on either another thumbdrive or a external 320GB drive (of the old fashioned spinning kind) because Ubuntu kept giving me cryptic failure errors before I even got to the partitioning stage. I did not want to install Ubuntu in a partition of my laptop's SSD for various reasons, mainly because I need the space for my Win10 OS and it's already at a premium.

When I tried to simply customize the USB drive installation, which is set up as "persistent" I also got some errors when trying to install languages and other programs (the latter did eventually install after a few failures, but not the languages), and then I run out of space and I had no idea how to increase the space. As an example, if I were in windows and I had a partitioned drive, I would simply save space on the Boot partition by installing new apps in the other partition. In Linux I have no idea on how to do that.

My ultimate goal is to have an external drive I can take with me and use on any 64bit computer in the home or outside (eventually, I'd create a 32bit version as well for old netbooks) and where I have installed a suite of apps and preferences similar to what one would find in Ubuntu Studio (which I also tested, but it was error city from the beginning, so I figured I can install the apps I need myself).

I have used several tools to create bootable USB thumbdrives. From YUMI (which I have used for a repair disk along with a few distros just for fun and practice) to other tools designed to work with a single distro.

In this new USB3 Thumbdrive I need enough room to install apps like Inkscape, Gimp, Music composition, video editing, code development and so forth without getting out of space error, plus a partition where I can save some files I may want to share, via thumbdrive, with my windows and Mac OS machines. The rest I can simply upload to my various cloud accounts, but the installation has to be able to work even without WiFi available, hence, I need some actual storage space for files as well.

I am not asking for step by step, detailed instructions, but more like pointers to other posts I might have missed, blog posts, "How to's" etc.

No Linux Distro I have tried so far has worked well enough just running off the USB thumbdrive. Regardless of how much persistent space I gave it.

Am I asking too much of Linux? Should I just buy another SSD and swap or find some other way to connect it? Would 2 USB thumbdrives work better? One for the OS another for Files? They are small enough these days.

Thank you.

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    You wrote "best" in the title. The best way to make a persistent portable bootable Ubuntu device is to start with a portable USB 3.0 SSD. It has the same form factor as a thumb drive and comes in different sizes up to 256GB. Then follow the instructions in this question: How do I install Ubuntu to a USB key? (without using Startup Disk Creator). However for the same money you could get a bigger internal SSD. – karel Feb 28 '17 at 05:15
  • Thank you for the reply. I ended up using something similar to the article you linked to. In fact, now I have a 64GB Thumb Drive that I partitioned in 2 with one half using YUMI and the other a partition I can use to save my linux files as an external drive. Windows only sees the first partition, of course, but I am using Google Drive and Dropbox to share any files I need on Windows. – Marco Conti Mar 15 '17 at 21:43
  • Then I have another USB where I proceeded exactly as illustrated in the post. In fact, I have one for Ubuntu and one for Ubuntu studio so I can have some good graphic, video and programming tools in a stand alone boot I can use on anyone's computer depending on needs. Ubuntu Studio is nice, but not as stable as Ubuntu. I might built my own "studio" version someday. – Marco Conti Mar 15 '17 at 21:54
  • One thing I didn't know was that there are SSDs with the same form factor as USB thumbdrives. I have never seen one, or I didn't recognized it as such. I happen to have a 256GB SSD (orphaned when I upgraded to a 500GB a couple of years ago) that I keep in a case and that I have used as both SATA3 and USB3 external drive, but it's not really handy to carry around on my keyring. I shall research that. What are the differences? and if they both go through USB3 ports is the SSD still faster? My Samsung USB3 Thumbdrive with YUMI is actually quite fast. – Marco Conti Mar 15 '17 at 21:54
  • The motivation for using SSD vs. regular flash drive is not speed but durability. USB flash drives wear out very quickly under the conditions of frequent read/writes associated with a complete installation of Ubuntu on the flash drive. – karel Mar 15 '17 at 22:24

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