IRL USA: Owning property comes with property taxes from your community, utility expenses, maintenance costs, home-owner's insurance, compliance with city ordinances, etc.
My grandparents owned their home and the land it was on for 40 years and barely managed to pay the bills with their kids, grandkids, and great-grandkids visiting or sleeping over often. My mom never owned a house until all us kids were moved out as adults, and even then her mortgage payments were 70% of her monthly income.
Medical bills in the US are insane. I went for a set of x-rays and a single tennis-elbow treatment. Insurance paid 50% max, leaving me with a bill for $500 out of pocket. I currently have no insurance, so a simple dental cleaning and checkup costs $150 out of pocket. Talking to my Dr. on the phone (not visiting) is $50/hour. Visiting is $150 up front + $500 per treatment/diagnosis.
Leading back to Hilda's home:
MC was born ugly, yes. Hilda went through hell with her husband(s?) and endured a lot of strife. She worked her big butt off housekeeping at home and for other people. Every penny she earned went into paying home bills, sending the kids to school, feeding and clothing them, etc. Which is why they only have 2-3 sets of clothes (like I did growing up - 3 shirts, 1 pair of shoes, 2 pairs of socks, 2 pairs of jeans and 1 set of gym clothes).
The game is set in a non-specified coastal region of the US. Lewd Town property taxes, home values, and city fees are insanely overpriced, making it prohibitively expensive to send MC to a dermatologist or get dental work done. Even Emily's situation - the doctor is a hack, mis-diagnosing her with just a 2-minute conversation and dumping some strange pills on her to make her feel happy.
If you played the prologue - Hilda asks MC for help paying the bills. That alone should prove just how dire things are financially. So spending around $1500 to get his skin fixed, $25k to get his teeth fixed (dentistry is insanely expensive out of pocket) is not even an option.
This is the point of how the game begins. We (the devs) hoped for empathy from players. Sure, we knew a few people would lose their shit over his looks. The point of him being so hideous is that he has nothing at the start - no friends, no money, not even looks. With ZERO opportunity to fix any of it himself. So that we can have a dynamic story of him becoming better, growing confident, becoming who he becomes in the Dark Path or the Good Path.