I'm thinking of a short term vacation rental (that'll just be about patching up a family property that happens to be in a heavily touristic area) and then in the future...

@Casey L Klauser sorry missed your meet up.

Example - Answering critical questionsYou must answer critical questions from guests in accordance with the timeline below:5+ days pre-stay: answer within 24 hours2 - 4 days pre-stay: answer within 12 hoursOn the guest’s check-in day and during their stay: answer within 1 hour (for messages received between 8 am and 9 pm in the property’s time zone).Examples of critical questions include; access instructions, arrival concerns, missing or broken key amenities, health and safety concerns, property location, outages, weapons, accessibility, and service animals.Note: You must provide a resolution to the specific issue or inform the guest when it will be resolved.

What am I missing.

No underwriter wants to lose their job over a "missed" item like that.

Take out loans to fix it up and then take out a mortgage at fair value.I could be missing something though, good luck!

If you’re making a good return you don’t want to miss years of income waiting on the market. 

Ultimately its hard for me to determine the value here with the data I already have and wanted to make sure I am not missing anything

The knowledge part was only one aspect of what I was missing.

Quote from @Jackie Liu: Hire someone to patch and paint the walls, then charge the tenant whatever that costs.