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Unless a client keeps very good records, tax reporting of cryptos is going to be a nightmare from hell, worse than reporting stock sales where basis is not provided. Because of the trading of one coin to another, the basis tends to get lost. On top of that, each coin has to be converted to dollars and each type of coin has its own conversion rate which varies on a daily basis. There is software designed to handle a lot of this, but you will still have to know when each coin was acquired, so records have to kept going back several years. The reporting is done on Sch D/8949 Some crypto coins issue a 1099-K, but usually for only large amounts. The 1099K only shows the sales and if this is not reported, the IRS will issue a CP2000.

How would someone, for the sake of discussion, be comfortable meeting the IRS data security requirements recently discussed here, while using a known outdated OS? Or, would someone be considered covered by E&O or other liability insurance if they elected to do something known to be unsafe (intentional act)?

At the top of Schedule 1 of the 2019 Form 1040 is the following question: "At any time during 2019, did you receive, sell, send, exchange or otherwise acquire any financial interest in any virtual currency? __Yes ___No" More work for all of us and more exposure of risk !

And one other note: we still have a W-XP machine - an ancient laptop. It's not connected to the internet, and never will be again. But it runs ONE program, that doesn't run well on more-modern operating systems, and for that one program it's worth keeping. (Yes, the program in question has an "upgraded" version - they removed functionality, and added multiple layers of complexity. We tried it, reverted instantly, and will keep the XP machine going as long as possible.)

I don't think MSE is baked into Windows, it is a separate application. Many expect at least some updates, but MS's official policy is no more (for consumers). MS has, in the past, provided updates, such as one for XP long after it was abandoned, but hoping is not really security (to me). I am a realist. Many will not change anything until forced. Dealing with a customer, today, who insists because S Corp Shareholder Insurance is deductible on the personal return, there is no harm not accounting for it properly as wages for withholding calcs. They are ignoring the payroll regulations. Another case of an owner/employee forgetting to treat all employees "hands off", with no consideration of the employee's personal tax situation. The tough part is they are telling me their CPA (and tax preparer) is relying only on 2008-1 for guidance, and is not considering the payroll processing aspects. I suspect their experts are only being asked about "tax filing", not "payroll processing".

https://www.computerworld.com/article/3514436/windows-7-end-of-support-separating-the-bull-from-the-horns.html

I think it just goes on Schedule D & 8949

Those hardware concerns are largely tied to age of motherboard and hard drives. Why put in the money when components get to an age where they mail fail? However, if you know you have a robust machine, and it meets the specs for W10, go for it. Just (as always) keep good backups!

All good here.

Made me do a quick count from my web site logs. (I don;t currently track W7, since it is still possible to be viable, although not at the consumer level.) As of 2020, I have at least 80 customers using XP SP2, XP SP3, or Server 2003 30 using Vista, Server 2008, or Server 2012 Not a large percentage, but for the data they are responsible for, should be zero. These are customers who are not going out of business (at least willingly) for 2020. Given my experience, the numbers will halve each year, at best. Programming wise, provided one does not use "out there" Windows API calls, there is no programming need to prevent use with XP SP2 or later. Other factors can come into play, such as my preferred installation software vendor has dropped support for XP, which will eventually mean my software will not be able to install on XP either. Like when DOS died, I will eventually have to force people to make a decision, by preventing use on certain OS's. (We only provide support and only test with current OS, and strongly suggest using only current OS.) It has only been about a year since someone asked about a DOS version, even though we stopped creating them in the last century... Going through something similar now, with installation CD's (caused by the Wayfair ruling, and the low number of those actually needing a CD). The reality of current payroll processing is an internet available computer is needed, making a CD not needed, although some claim - despite web site logs showing differently - they cannot download because they have no internet access where they are. As an old timer once told me (back when I was not the old timer), "Only worry about the 80%. If you try to handle everything the last 20% ask for, you will muck things up for the 80%." I would add those last 20% are the ones who keep you up at night, and the ones which could be costing money instead of earning money. The ~110 count are not even a tenth of a percent (thankfully), so while I absolutely appreciate their business, when I have to force them to move up or along, it will not (much) make me lose sleep. If I have a point (It is first half of January, my mind is like yours must be April 15 or whatever your deadline dates are), is some will always be pound foolish, and some will get away with it. But, as good stewards of our customers, we must be penny wise.