Should I buy another house with my parents?

Hey all. First time asking some questions here. If this isn't the right place then I apologize in advance.

I'm 33 (M) and have owned a house for the last 4 years. I have a mortgage of $60K, a low interest loan of $10K, and stable job with a salary of $80K/year with possibility of going up to $100K in the next 5-10 years in this field. My 401K and IRA are both fully funded and I have about $50K saved up in the bank.

My parents have a fully paid-off house and are in a similar situation with about the same amount of saving. Their combined income is around $100K/year and will probably be working for at least 5-10 more years.

I have a great relationship with my parents and we've been talking for a bit about buying a house together to rent out. The tentative plan is we'll split the cost of buying and renovating the house. After that I'll be in charge of looking for tenants and be their contact person while my dad, being a handyman, will take care of maintenance for the little stuff. We'll obviously hire contractors for bigger things.

I have some experience subletting my house to roommates but no landlord experience. I obviously intend to learn and research heavily before going forward with all this and to save up a bit more money. My hope is to plan on buying it in a year to a year and a half.

To further add another layer of complexity I've been dating someone for a while now. She has about $150K in student loans that I intend to take on when we get married in the next 2-3 years. Would it be wise to purchase another property while still paying off my current debts, paying a wedding, and taking on girlfriend's student loan as well? Also, what about going into business with family members?

Any help or insights would be appreciated. Thanks!