And in my opinion, his book covers everything a newbie needs to understand: from asset selection, to evaluating sponsors, to capital structures.

I can't remember the last time a tenant's pet cause damage that wasn't covered by the deposit. 

This is a very common agreement, in your space your problem and they also should have insurance that if its extensive insurance would cover it. 

You might be covered if its the second one. 

Keeping this as a rental would not cover the mortgage (we'd have to pay ~1500 a month including utilities) and we can afford the extra payment, but is it worth it when looking at appreciation?

So make sure you can cover both loans for awhile. 

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.

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

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..