On the timer, the Song of Reverse Time (play the Song of Time backwards) halves the time of the 3 days, which made it rather easy to do everything you need to do in a cycle. Song of Soaring allows you to get to all the places you need in that cycle quickly, notebook in the remake keeps track of everyone's schedule so you'll only need guides for like, Anju and Kafeki, and the Song of Double Time gets you to those times quicker. The only time you'll feel threatened by the timer is likely during the Great Bay Temple.
For the 'losing your money' issue, there's a bank where you can deposit your money so it stays next cycle. As for ammo, it's generally easy to come by and arrows are pretty cheap. The only thing money-wise i'm ever worried about was buying mana potions each cycle, which aren't all too expensive anyway.
I personally loved the timer system. The ways they set it up allowed for each day to feel like an actual, real day - shops were closed on different days, people got progressively more scared as the third day approached, different events and such happened on each day, etc. Clock Town felt so alive, because everybody seemed to be going about their lives as if it was an actual town - you could see the construction work being done (and watch it be finished), you could talk to npcs each day and watch their mental state change (personal favorite is visiting the "fearless" dojo mentor in Clock Town about an hour before impact), go to a band that is only coming on a certain day, fend off an alien invasion before they mindfuck Romani and thus you can do different events on the farm for the next two days... I adore the system and I still do today. The game isn't supposed to feel like Ocarina - a cheery, free, adventurous game. It's supposed to feel macabre, hopeless, and claustrophobic. The timer is probably the biggest reason why it has such a dark atmosphere - it's supposed to make you stressed and hopeless at times, and that's why I love it. Easily my favorite Zelda game.
Also as for the Souls series - "single mistake screwing up an hour of progress" - i don't really think so. I've played through both Bloodborne and DS3, and they gave you checkpoints generally near each other, and easy to memorize attack patterns/routes so dying once or twice wasn't a big deal. I can understand being anxious about getting your Souls/Blood Echoes back, but in BB I can get about 300k in 15 minutes with chalices and in DS3 there are multiple grinding spots. Can't say anything for DS1 though.