Ok, if I understand your situation .... not only did the principal amount increase (when you made the subsequent loan) but also the payments were irregular (sometimes twice a month, sometimes every 2 weeks).
The Quicken loan wizard is REALLY set up to handle regular, recurring amounts (your mortgage or an auto loan, for example) where the payment is made on a recurring, predictable UNCHANGING basis, and the principal only changes due to regular payments.
In short, you're going to have to calculate this manually, probably using a spreadsheet, to calculate for each payment how much of it was owed to you as interest and how much was applied to reduce the principal. The basic formula for calculating interest for each period is: Interest-Due = Principal-outstanding TIMES Interest-Rate-for-the-period TIMES time.
Principal-outstanding is, initially, the amount of the loan. Interest-rate-for-the-period is the agreed upon rate divided by (12 times the number of agreed upon payments -- i.e, 24 if paying twice a month, 26 if paying every 2 weeks). Time is the number of days since the previous payment, divided by 365 or 366.
The total payment received minus the interest-due is the amount that reduces the principal, thus producing the principal-outstanding amount for the next period.
So, the columns that you'll need in the spreadsheet are: Date, Action, Principal-outstanding, Interest-due, Principal, New Principal-Outstanding.
After you create the line for the first payment, you just copy it down (editting the date field as you go) until you get to the point of the subsequent loan. At that point, you'll need to slip in an additional line to reflect the addition to principal of the subsequent loan. Be careful with the immediate next payment calculation, it can get a bit weird.
BTW (curiosity got the best of me), are you Canadian? I noticed the use of the word "Cheque".