1. In answer to your first question about separating the two vehicles into their own "entities" in TurboTax this year, a most definite yes. IRS requires that you track (for each vehicle used wholly or in part for business) track beginning and ending odometer readings, miles for each business trip, business purpose, date and time. Do not merge vehicles, keep good mileage and expense records on each vehicle, always.
2. I recommend, for this year, that you dispose of all the "generic vehicle groups" as of 1/1/2019 with no gain or loss recognized. Make note of the book value, and allocate it based on the original purchase price or fair market value of each remaining vehicle (be consistent) and then "purchase" each vehicle in TurboTax at the allocated book value (adjusted cost basis less depreciation) and continue deprecating them from that value forward. If you used mileage, you will need to determine the Equivalent Vehicle Depreciation. (Please see the Depreciation section of this article: Business Use of Vehicles) in order to determine the book value of those vehicles.
3. You need to go back and amend your previous years' return and reconstruct your business use and personal use of each vehicle and report them correctly.
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