>> I have a hard time spending, to the point where I would often procrastinate on buying things that I know I’ll need in the future.

Well, what I noticed is that I go to great efforts to avoid buying me some stuff that would make my life easier (say an electric bike or a better computer). Month starts, I get my paycheck and every day I fend off the desire to buy the stuff I want/need. And then come the bills. Like some surprise "regularization" gas or electricity bill that costs more than the item I didn't buy. If it's not that, some darn thing breaks and needs repairs. And if it's not that, kid has to go in some school trip, there's some birthday or wedding we have to attend, someone asks me to lend them some money (coze they know I save) or some other event happens and requires a ca$h infusion.

By the end of the month, money's gone and I haven't got nothing. At some point working just to pay bills and expenses makes Jack a dull boy. So funk it, I buy that stuff AT THE BEGINNING OF THE MONTH. And when shit arrives demanding money I can truthfully say: "I don't have any money left". But at least I got the thing, opposed to neither money, nor item.