I dunno about "best" way, this is certainly "a way"...
Assuming you have a spreadsheet with 2 columns - column 'A' contains hte old url as a relative path, column 'B' contains the fully qualified destination url - you should be able to use the spreadsheets concatenation function (ive done this for nginx rewrites, but it should work for IIS) to assemble the redirects, then copy and paste them into the web.config.
Start with a simple rewrite
<rule name="Redirect 1" stopProcessing="true">
<match url="/source.html" />
<action type="Redirect" url="https://www.example.com/destination.html" />
</rule>
(you will need to "flatten" it into a single line first)
Split the rule into 4 parts <rule name="Redirect
, " stopProcessing...url="
, " />...url="
and finally " /></rule>
(ie leave space to number the rule, and remove the source and destination urls), and paste these 4 fragments into cells E1, F1, G1 and H1 in the sheet. In Column 'C' enter numbers 1..200 (rules need unique names), then in Column 'D', (in Excel at least) enter
=CONCAT(E$1,C1,F$1,A1,G$1,B1,H$1)
(E$1 .. H$1 are the 4 cells that contain the fragments - the $ is to stop Excel from incrementing the rows).
Copy that formula down the page - volia