1: You are assuming here that being prepared for the worst dilutes or even negates good intention and/or tawakkul in Allah. And that’s a dangerous assumption. A muslim works with reality & does not do so naively or idealistically.
Take the Hijra for example.
The seerah is clear: SAW meticulously planned for Hijra while waiting for the departure order.
Aside devising a decoy plan with Ali RA sleeping in his bed, he, SAW, had planned for the exact cave to hide in, which is smartly located in the opposite direction of Medina. He’d..
Similarly, a muslim (man or woman) planning for marriage (anything) should consider realities on ground & do their best to prepare for bad outcomes, while trusting in SWT
May SWT provide us ease
Bissalam.