This helps determine the appropriate asset allocation.

Unfortunately, you have to hit them at the 'right time' but that's impossible to do unless they're in a difficult situation and want to get rid of the asset. 

You can usually use bonus depreciation against the asset assuming it will follow the short term rental loophole rules of 7 days or less average stays. 

Educating yourself about different investment types, asset allocation, and risk management will empower you to make informed decisions.

In no way does a $4,400 repair or fence replacement extend the life of the asset and it is minuscule compared to the asset’s value.  

For example, I believe Nest and Ecobee digital thermostats allow you to put a low/high floor on the temperature so tenants can't put it below or above a certain temperature.Finally, your lease should include a clause that says tenants are responsible for repairs if they abuse or neglect the property.

I'm more interested in just growing assets.   

Someone told me if I put the property in an entity's name, I could sell the entity with assets and the deed would not need to change.  

For lenders/banks, quality vacation rentals are clearly a unique and reliably performing asset class..For investment properties these lenders typically require a minimum 20-25% down payment but since there is higher gross revenue, the investor can often qualify for a higher loan amount.

You maybe able to suggest they invest in another asset with some of the money.