Hellboy, one of my saves (best yet) is on day 49 and I haven't spent a cent on castle improvements. They just raise your tax/upkeep and stop you from making money. Buy some repair hammers and skip the upgrades.
While I agree in some ways DeepThough, not being able get past level 10 on multiple tries is lacking in skill. I've never found a problem until closer to level 20. There is some strategy to this game, like how you spend your money, but there is luck too.
There's a little too much luck on which weapons you receive or show up in the store. If I get a couple bowguns in the hands of my party, things get a lot easier. Other times I'm stuck with a LVL1 weapon the entire time.