I have a friend who always try to pay with post dated checks for amounts that are above 10,000 pesos (around $200). Her check is 30 days after so that means she will be using the bought item for 30 days before the payment takes effect. It's a Neat trick that she applies and fortunately most of her purchases are like that. I'm now thinking if that trick can also work for me. But my husband cautioned me because I work in a bank and that might not be a good practice for me.
Before when I had still a small business I had a bank checking account and I am using it for business purposes only when I am paying my suppliers. But I am never using it to pay for my personal purchases or obligations. It is still my choice to always pay in cash when ever I want to buy something. And one thing I don't like the idea that I had already use or consume the items that I bought then it is not yet paid. You can never tell when you issue a postdated check and then when the date of issue falls due and you do not have the money to fund for the check that you issued then it will be a problem.
You aren't allowed to officially pay with post dated checks, and before debit cards people did do this only for convenience and they had a guarantee number. Many places don't accept checks in the UK any longer, and I only write them for my dad who still prefers them, but when he sees there is a charge for checks and none for debit cards he will go for the debit card. In the UK at least if the check is post dated it won't be accepted, because it is now considered a tactic of fraudsters.
I'm sorry that my answer won't address your question/dilemma. But I just have to put it out there; I personally hate checks and feel they're so dated LOL Like Theo said, checks are now being phased out in the UK, and quite frankly, I wish the whole world would follow suit. I can't even remember the last time I had a check book, let alone used one. It's such a shame that they are still a thing here in Botswana, a country which sadly continues to embark on practices that waste paper and create a lot of unnecessary work for staff.
Most of the times, it's the installment sellers or supplier that require post-dated checks because of the convenience and added assurance of collection specially if they are dealing with businesses. Otherwise, they'll simply accept dated checks at the time of collection. Businesses prefer to pay in checks because it's easier to trace in case of dispute as they'll get a copy of the used checks and they usually cross the check so it will be deposited under the name stipulated in the agreement between the supplier and buyer. Checks aren't that much used in personal transactions except probably in utility businesses which can just cut off your service and charge you under bouncing check laws. You can't just decide to pay post-dated checks, that is all up to the seller or supplier.
I won't accept a post dated check or allow customers access to the item until I am able to cash in the money. Tell me what happens if the check bounces. If the customer expected some deposit in the account before the date assuming reason for the post dated check was lack of money at the moment, what happens if no deposit by the date. I think this is a complex way of making payment.