I can offer the following:
Do not underestimate computer illiteracy and be prepared to never mock that illiteracy. Most of the people that I have thus far interacted all freely and readily admit their computer ignorance. They also do not want to know how to "change the oil." Most users mostly surf the web, check email, waste their life on Facebook. A few are more adventurous and will stream a video or two, usually of the youtube variety. Most do not know about streaming music. Most do not know anything about ripping CDs or DVDs. Most who stream Netflix do so from a network-enabled TV and not the computer. Most have never used a keyboard shortcut. These folks are good people, enjoyable to have a conversation, skilled in other areas of life. Just expect little in terms of computer knowledge. Be prepared to meet them at their level and not your level.
Most of the people migrating from XP have maturing hardware. I ran into one customer who has a 20GB IDE drive and the drive was not full. These folks do not know what they are missing so don't enlighten them. Just work with them at their level.
Although most of these users do not use unique software, a few do. Right now I am working with a customer to test a proprietary Windows app in WINE.
Thus far we have not run into the classic MS Office/Quicken/QuickBooks/Visio dependent user. We don't really expect much of that because those types of users are business users and at the moment don't fit our target audience. I do nonetheless spend time thinking about those users and how we can help them when that day arrives. I have several ideas but at the moment nothing concrete to offer.
Most of these users have no concept of man pages or online forums. Most do not know how to search the web to help themselves. Few will remember to use email. Tell them about online forums as a means to find help, but don't berate the point. They use the phone to ask for help. Tech support over the phone is challenging but that is how these folks do things.
Don't try to educate them about all of the different desktops. The result is glassy eyes. Just install whatever desktops you want to support. That each desktop has a goofy geek name is irrelevant to them. They don't care. Currently we are only supporting Cinnamon and Mate. The latter is for the really old hardware.
Don't try to educate them about 32-bit or 64-bit. Over their heads. Currently I am using a basic 2GB RAM threshold and CPU model to start my decision-making as to which version I install. However, there is also gut feeling after booting into the new system on the old hardware. When in doubt use 32-bit. These folks do not know and cannot tell the difference.
The default desktop with just about any distro expects command line usage. That is a sad statement. The die-hards and the arrogant believe Linux can't be used strictly from the desktop. One of the first things I did was modify the default desktop and removed the terminal from the panel and top levels of the menu. The terminal remains available in the System Tools/Administration menu. I use the terminal all day but not for these people.
The default desktop is designed by geeks for geeks. There is a flawed philosophy floating around to "maximize screen real estate." Thus panels are too small, sliders and scroll bars to narrow, fonts too small. Watch a non geek use the computer with such defaults. They start squinting and craning their necks. So I fix all of that too.
These users know nothing about security and have no exotic needs. (G)ufw is sufficient. Allow all outgoing and disable all incoming. Disable all services.
Eventually I want to provide SSH/VNC support to help customers. I intend to create a one-click script that will start the respective service only as needed and vice-versa, stop the service. Everything must be GUI for these folks.
As all of these users are migrating from XP, install the ms-core-fonts package.
Most of these people will not use 80% of the pre-installed apps and most are likely to never even look at the apps. Thus one-app per task is sufficient for these users.
Most of these folks do not use user accounts. Most do not understand them or even know they exist. Most expect auto-login, even in multi-user homes. They all use the same computer and same desktop.
I stopped installing from the DVD after about two attempts. Installing from a DVD is painfully slow. After I fine-tuned my customizations, I made partition images and now install from those images. I use gparted and the grub2 super disk to complete the installation.
I am writing an installation shell script to help me automate the process after copying the partition images. The script will help me migrate app settings as well, such as Firefox, Chrome, Chromium, Thunderbird, etc.
For Outlook/Outlook Express users, install Thunderbird in the Windows side before migrating the user to Linux. Thunderbird imports Outlook/Outlook Express very well. I have read this only works with OE up to the 2010 version and but we are working only with XP migrants and thus far is not an issue.
Likewise for the web browser. I install Firefox and import the IE settings in Windows.
I have read many times through the years how challenging installing Linux is for newbies. We needed actual Windows partitions to simulate the same setup as the customers and I must say, installing Windows from scratch is hideous, painful, slow, and limited. There are no options to partition a drive. Installing an original XP disk and then SP2 and SP3 takes about 1-1/2 hours. You're screwed if something goes wrong because you get to start from scratch. Familiarity might indeed breed contempt but I'll take installing a Linux system any day over Windows.
I am working on a basic backup strategy with rsnapshot, cron, and a separate partition. XP users are accustomed to System Restore and expect something similar.
We use a second drive rather than repartition. Most of these users do not have hard drives large enough to repartition. A second drive allows retaining the XP system untouched, which provides the users peace of mind and a drop-back recovery plan. I explain that repartitioning is doable but they would not save money because of the time involved to backup XP, defrag, resize, and retest. Thus far we have not run into a laptop user where a second drive is not possible and we would have no choice but to repartition.
As most of these people have aging hardware, proprietary video drivers have not been a critical need.
We have not attempted to make the desktop look like XP. All of the users accept that they are not using XP and are prepared for a desktop that is mildly different --- but works very similarly.
We have not started any training classes. When we do we more than likely we will focus only on cross-platform apps and a basic desktop class. I do not foresee ever having a class on the command line. While we might charge a nominal $5 or $10 for the classes, we just as possibly might charge nothing and use the classes as "loss leaders" to encourage people to let us install Linux.
Most distro user guides waste half the document with installation steps and command line usage. I have always believed installation and command line usage should be separate documents. This is the geek mentality shining bright. As we provide these systems pre-installed and "hide" the terminal, we plan to rip those sections from the user guide. I plan to write our own user guide and most of the guide will be task-oriented in the form of "How do I...."
We plan some day to post tech support web pages and an FAQ.
Pricing is regionally dependent. We are in a rural area. Folks are not rich. They can't afford new computers. If they could then the XP EOL would not be an issue. We provide a new 250G drive that is about 4x times more than they need, a demonstration, an assessment, installation, migration of user data and two hours of tech support. Use that information and a base rate palatable for your region to determine a fixed fee.
Although I am still fine-tuning the installation process, my original estimate of two hours turn-around still seems realistic. Currently I am spending more time than that because I am working hard toward automating as much as possible, but I discount my time toward startup "R&D" costs.
The demonstration is done at the shop. We have a dual booting XP/Linux system. Most are not interested in cool features. Most are interested in the basic pointy-clicky things. Most are interested in migrating data. Most are annoyed by the stupid popup reminder that XP has reached EOL. Most are concerned that the new system will be secure. So the demo period is not exhaustive and I don't try to impress them with anything.
Assessment is important because that is the only way I can know what problems I might experience. I won't take a customer's computer until I am confident I can migrate them. A current customer has a non-negotiable need for a proprietary Windows app and I had to test the app on my own in WINE. This was the first WINE need and I again discounted my time and effort to startup "R&D" and improving my knowledge base. Assessment includes peripherals. I note the model numbers and return home to surf the web for potential problems. Surprising to me, all-in-one printers/scanners/fax/copiers are popular.
Don't forget "unseen" peripherals, such as web cams and digital cameras. Always remember that in Windows these peripherals "just work" and these users lack the computer knowledge to understand or appreciate why they might not work in Linux.
Be prepared to recommend certain users stay with Windows. I did that many weeks ago. The person was deeply locked into various forms of vertical software.
I probably could charge extra for a lot of this research but I am willing to live on the proverbial shoestring during the startup phase and tally my time and efforts to R&D.
In summary, Linux is still designed by geeks for geeks. Be prepared to think and act differently with customers. They are not geeks and have no aspirations to become one or play one on TV.
Last note: this is the Slackware forum. As can be learned from reading the entire thread, many topics have been covered beyond my original post. We are not using Slackware for our venture. We are using LMDE. (I personally still use Slackware.) There are folks in Slackware land trying to massage the base Slackware into something more palatable for non geek users. As I shared previously, when I am more experienced with customers I hope to return to evaluating how I can bring together these different derivative efforts into something non geeks would enjoy. Slackware is not alone in my observation. Currently all distros are designed by geeks. I don't foresee usability changing much until distro maintainers focus on non-geeks rather than rely on fellow geeks for feedback and back scratching.
I too am looking for the experiences of others.
So far I am not making gobs of money but am having fun meeting people and find the whole venture stimulating and challenging.