I grew up in a house built in 1894 (or there abouts) and my parents did not have any major repair issues.  

Clarify this with an accountant for sure because I’d hate for your parent’s wishes to be missed simply because of a misunderstanding there.As far as negative cashflow vs positive . . .

I know the general tips such as having parents co-sign and having a cleaner or someone checks in every 4 months or so to make sure the property is being maintained but wanted to see if there were others, especially in my local area.Should I rent out by the room or rent the entire place out and have a designated lead that responds to me?

He has been living with his parents since he got out of college.

They can pocket the money and grab one from their parents, buy a used one for $60 or put it towards a new one that costs $300 it doesn’t matter to me what they do.

Currently analyzing a quad-plex deal for my parents.

My parents were in the housing program.

From a legal perspective, you also might want to consider having the tenant sign something that waives their right to sue the landlord if they get hurt from something in the house (for example, their parents can't sue the landlord if their kid drunkenly decides to dive head first into a door).

Hi, My parents are Deltona, Fl. residents selling a place in NY.

Unfortunately, the family business recently shut down and caused my parents to go into bankruptcy in 2020.