Growing up, both my parents had been landlords for periods of time, and I've experienced first hand what bad tenants can do.

Listen to your gut, not your parents.

The other issue is charities in the area will not take donated buildings at this time. 

Many of them continued to try to remote-manage the property and made various other bad choices.Cue present day: these duplexes are always in bad shape, always run by incompetent aging LLs who wish their parents had just given them some stock in Ma Bell or General Electric, always need a lot of TLC from good handymen, who are fewer and fewer in number.

I have this super huge fear of buying something that I thought was good, finding out it will cost WAY more, and then my parents and everyone around me calling me a massive failure.

My first investment property is a 5/2 SFH in a college town so typically parents are paying the rent.

The best ways to combat this I think would be, a.) joint venture with my parents (they already own 2 rentals) b.) get a large multi (5-8 units), or c.) possibly get a mortgage in my parent's name and pay them extra interest.Which would you guys recommended or avoid and why?

Parents paid cash at closing and I pay them back a mortgage each month (they wanted the interest income and I liked the smooth closing).

Come to find out even though parents been deceased for over 15 years, probate was recently done to get into the executer name.

My tenants’ parents visit occasionally from out of the country and stay for a few months at a time.