Making 2 separate "Check Pay" transactions to the same memorized Payee with 2 different catigories.

Ripperdan

Using Quicken Classic Deluxe.

How do I set-up and implement 2 separate "Check Pay" memorized transactions to the same Payee with 2 different categories?

As an example, on the 1st of the month, I want to send a $200 check to my church (Baptist Church) for the "General Fund" with "General Fund" showing in the memo field.

Then, on the same day, I want to send a $50 check to the same church (Baptist Church) for the "Building Fund" with "Building Fund" showing in the memo field.

NotACPA

Why can't you use a SPLIT transaction and make it a single check payment for the total amount?

That should cause both categories, and the respective amounts, to show in the memo field of the split

UKR

As suggested by @NotACPA, sending 1 (one) Check Pay check to the church seems to me the best solution, especially when considering that you only have a limited number of free Check Pay transactions per month. Exceeding that limit, additional monthly fees kick in.
Indicating something like "$250 GenFund, $50 BldgFund" in the Account Number field of the check pay payee should make it possible for the church to record it correctly.

In Quicken you can set up and use one Scheduled Reminder to automate the process. When setting up the Reminder remember to select the checking account to pay from and also select the option "Allow paying with Check Pay".
Categorize in Quicken as needed, with or without a Split.

For more details about Check Pay please review About Check Pay (quicken.com)

If necessary, set up two reminders.
If Check Pay fees become an issue or you have problems with using Check Pay to make 2 payments to the same payee that even Quicken Support can't figure out, use those reminders to write and mail (or print with Quicken) 2 paper checks.

Ask the church if they allow direct deposit to their bank account. You might be able to use Quick Pay instead of Check Pay.