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If you have to file tax returns for several people, using the desktop TurboTax software will probably cost less overall than using TurboTax Online, unless some of the returns are simple enough to use Free Edition Online.  

If the plan uses value in the 401(k) to satisfy the loan after you have left the company, it would be done as an offset distribution, not a deemed distribution.  A deemed distribution does not satisfy the loan, it just makes the outstanding balance taxable.

When you use online TurboTax software you get one return per fee.   Each return needs its own account and user ID.   If you use the same account and user ID for a second return, the second one overwrites the first return and it is lost forever.     https://ttlc.intuit.com/community/using-turbotax/help/how-do-i-start-another-return-in-turbotax-online/00/25596   Not sure what you mean by "multi-print"----when you use online software the fee is the same whether you e-file the return or mail it in an envelope.   Printing and mailing the returns does not save you $.

Yes, with some limitation.   This is not a casualty loss, it is non-business bad debt.  This is deductible as a capital loss on schedule D.  See these links to start. https://www.irs.gov/taxtopics/tc453 https://turbotax.intuit.com/tax-tips/irs-tax-return/how-to-report-non-business-bad-debt-on-a-tax-return/L1mUzQFtB   The first point is that the debt amount must be final and uncollectible, and you must make every reasonable step to collect.  If the contractor is in bankruptcy, you must contact the court to be listed as a creditor.  You can't deduct any loss if there is a possibility of collecting.  This might mean that you can't deduct the loss until the bankruptcy case is closed.  For example, if the case does not close until 2026 and you recover $5000, you could deduct the remaining $51,000 on your 2026 tax return.   If audited, you must be able to show the IRS how you determined that the debt was uncollectible and the date it became uncollectible.   Then, this is a capital loss on schedule D.  It can offset other capital gains, such as from sale of stocks.  If you don't have capital gains to offset, you can deduct $3000 in the first year, and the rest carries forward, and can be used to offset future capital gains or be deducted at $3000 per year until it is used up. 

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Not talking about specific forms or actual filing, just getting data in as placeholders to do a calculation sufficient to make year-end decisions.  Obviously we don’t have 1099s or W2s yet, either.  But we can estimate if we have a place to enter our estimates.

TurboTax gets no information from the IRS after you file your tax return, so no one at TT knows what the IRS has changed or why you now owe.   The IRS should send you a letter with the reason(s) they say that you owe.