Best way to associate bank autopayment to update loan and asset account

I'm new(again) to Quicken and trying to setup my accounts. The goal is to track net worth/assets/liabilities and eventually budgeting.

I'm trying to determine how to setup for a scenario where I have an asset with a loan against it and the payment is made automatically from my checking account every two weeks.

I can set up the loan linked to an asset easy enough. The problems seem to arise when I download my transactions from the bank, if I do a transfer to the loan account it doesn't split the interest/principal. 

Also, when setting up the loan, Quicken asked the start date, initial amount, interest rate, etc, etc and the next payment date. Which I entered, then I downloaded historical transactions from my bank account, if I try to enter those against the loan, it causes the remaining balance to be incorrect.

Is there a documented method for initially setting these types of situations up in Quicken please?

Also a method to apply a payment automatically paid from my checking account to work as a payment and autosplit the principal/interest properly?

Seems like a common scenario, but I've yet to find a "convenient workflow.