One note is that if the property was helping cover my costs of living while I house hacked it I wouldn’t worry about negative cash flow while I resided there.

You have to do the work on the front end and vet out who you are listening to about the subject you want to learn about.

One was making an extra $600/month while covering all of his household expenses with just 3 PadMates. 

Quote from @Bruce Woodruff: So that's 7 months......now investors will have to add a bit into their flip budget to cover the extra 3 months (or so) holding costs... will make overall costs go up though... 

Could I send you a DM on the subject?

I think you'll also find that even if he isn't liable for the debt, his interest in the property is subject to the lien of the mortgage. 

Future AppreciationLynchburg’s market has seen about 5% appreciation recently (4.3% Sep 2024), meaning your property could gain around $110K in value over 5 years, helping to cover renovation costs.

That is where the letter of the law stands and to have you covered..

I'm having trouble finding any real solid information, experts, or sources on the subject, so I figured I would reach out to the BP community. 

Offering $450K would leave room to cover the $50K in repairs, and since market rents support a solid increase after updates, this could boost your long-term cash flow significantly.