Always post an invoice/expense as per their invoice/expense date. Make the payment as per date it was paid.

If invoice and payment made on same date then use the purchase module using the Pay from (instead of pay later) and select the method of payment.

Since you have had formal training in bookkeeping I'm sure you know abut the rules for allowable meal expenses and how to record/track gas expenses along with km logs etc if required.

If you get audited and the auditor wants to see a  receipt for gas that was entered in your books on this date for this amount would you be able to find that receipt immediately?

Rent and utilities are to be posted as vendor invoices on the date they were incurred - rent is usually the first of month, services are to posted as sales invoices thru Acct Rec to same name - then payments can be made thru contra account between customer/vendor if one is offset by the other. Then a cheque can be produced for the difference.

How are the customers paying for subscription to software/cloud storage? is it thru your client's website?

I'm not sure what you mean by " pay expenses tab to input everything so I don't have to create a hundred plus inventory items for invoices" - if you mean that a supplier's invoice can have 100 items on it you can still post by invoices but you don't need to note every items on the invoice unless you are using inventory module.

Are you getting vendor/supplier stmts every month so that you can reconcile each month to ensure all invoices have been rec'd.

Are you getting bank stmts and credit card stmts so that you can reconcile these every month?

I do make sure all expenses are put on the day they were incurred/paid, no matter the way I am entering them.  

I can most definitely hand over any receipts if they are needed as I refuse to enter anything without a receipt.  

Rent is being done through the vendor just using the cash clearing account as a way to make sure it is tracked even though no money is being transferred.  

The customers are paying for their subscriptions through the services they are receiving as a whole (like a bundle package). So it is never really split apart on their bill it is just a part of the service they offer.

To get to the pay expenses option I go to the Vendors & Purchasers dashboard then under the payments section the drop down menu has a pay expenses tab. I select that and use that right now. Should I actually be setting up inventory items for everything such as Internet, phone, business cards, benefits and run them through an invoice instead.  My current method has allowed me to still put together a detailed payment without creating an invoice every time. Especially since by the time I get them they are already paid so I don't have to ever worry about creating a pay later invoice. (hopefully this makes more sense)

Receivable invoices are created every sale that they make, I don't do that but they do and they are very particular on that.

I get all the records to do a proper reconciliation at the end of each month (I am working on some of their backlog right now, they have several months of undone books). Thankfully they are organized in the sense that they only ever use 4 sources for payments and those sources are only ever used for business so that is pretty straight forward.

You definitely don't need to set up inventory items.

It is not mandatory to date expenses/bills on the date that they are incurred on a day-to-day basis. At the end of the year, the accountants should make an adjustment for outstanding costs (accrued liabilities). You have several years to claim the HST ITCs on purchases, so that's not a problem either. If the bills from the suppliers are paid as soon as they come in, then it is perfectly acceptable to record them all as pay expenses with the date of the payment as the transaction date.

Typically, I tell people to use the purchase invoice feature only if they have 30+ days payment terms with their suppliers that they do take advantage of. That is to keep proper track of how much is owed and properly match the costs with the revenues. I doubt there is much need of specific cost timing in this particular situation.

The timing of the sales is more important as CRA requires that the HST charged on sales is reported in the period in which the revenue is earned.

Using Pay Expenses/Make Other Payment is not wrong but it does force you to use cash basis accounting.  Some people do that to catch books up quickly but have to do accrual entries at least at the end of the year to get the expenses in the proper period.  I prefer using Purchases invoices and if the payment was made the same day, then change Pay Later to the method of payment, etc.  When the payment is not made the same day, I then go to Payments (I usually keep the window open all the time) and make the payment for the proper day.

I like to work in reality as much as possible and if the phone bill is dated Jul 28 and the payment is made by the owner via internet payment in Aug, then the payment entry has to be done separately from the invoice because that is the reality of the situation.  The expense is for July and the payment will hit the bank statement in August.

There is no need to set up inventory to use the Purchase invoice module.  On any line item, you only need a minimum of three items.  The dollar amount, the account to be posted to and if sales taxes are applicable, then you use a tax code.  If you wish to enter a description (sometimes a really good idea), quantity, unit price, go ahead.  It depends on if the information will be used in the future.  Recurring entries are good for entering standard things that rarely change.

What people do not realise is that the Make Other Payment option is entering an invoice just like the Purchase module but the screen looks like a cheque to fool users into thinking they are just making the payment.  But the expense is recorded on the same day and that is not always real.  If it is real, there is nothing wrong with using it (though as I have said, I don't).  If expense and payment dates are not the same period and you use it, then you need to make sure you do the proper accruals for at least year end, sometimes monthly depending on the owners.