I hire local professionals for inspections and cleaning, but even then, I’ve run into issues where things were missed because I wasn’t physically there.3.Tools: I use software like Tenant Cloud for rent collection and maintenance tracking, but no tool can replace having someone who can physically check on properties.

I’ve never had difficulty filing a claim with Airbnb as long as I showed the broken item and the cost to replace or fix it. 

A replacement has not yet been identified.

Here they all start with "Are you aware of any XYC.." and none of them are asking about previous repairs or issues.I understand that you are concerned, but honestly, if the water damage was resolved, the soaked parts replaced, why would it matter any longer? 

but if you have a view on active vs. passive income.my goal is to have income from multiple sources, ideally part time work that i enjoy is a component. 

Many unnecessary things are repainted, redone, replaced, and rebuilt.

I have yet to complete a walk-through of the property and see what renovations may be needed (potential for HVAC and interior, but from my understanding the roof and windows were replaced within the last 7-8 years).

If the sale is for $600K then you need to purchase $600K of replacement investment real estate. 

When I replaced the furnace a couple of months ago, I also installed a new 7 day programmable thermostat.

To ensure my replacement property value is at least $600k, I was considering putting the remaining $100k into a DST.