For this: "and they give them a 1099, Line 20 "other deductions" would be the appropriate place to report that deduction?"

Not necessarily. You are still confusing Who I hired with Where to report it. They are two different requirements that you will need to evaluate.

Tracking = What you hired someone to do is reported for what it is: They do repairs or maintenance or improved your asset.

Reporting via 1099-Misc = Whether the name (not a corporate entity) falls under the reporting requirements; and, whether the reason (a cost of a service and not for products, but not from a medical provider, and whatever else is in the 1099-Misc regulations) falls in the reporting requirements for a name that also is reportable. This part is not your Business Expense or Asset Improvement or Banking. It is Reporting.

Let me try one more thing: For everyone you Pay, you put a gold star on their forehead = the Reason you paid them is flagged and tracked. But, some of these people are Subject to 1099-Misc reporting. That is not "how I paid" but "that I hired this type of entity for that type of thing." It is Informational. Not Financial. Not everyone with a gold star also gets a 1099-Misc.

If you hire a landscaper or janitor, and that is tracked as Other Expense, than all of that is Other no matter who you hired; it doesn't matter that there also is a 1099-Misc or not.

The 1099-Misc doesn't change what you paid for.