I did not have the funds to buy them all out at the time other wise I would have..

In a scenario where the landlord resides in the same building, It may be wise to hold off on making substantial investments in the apartment where the landlord plans to reside for the first 3-4 months,This approach can help prevent any perception of discrepancies in the living standards between landlord and tenant.

Agreed, it makes no difference taxable income-wise to supercede the return.

Word to the wise, in doing life estate planning, include ALL properties.

They know exactly what they are getting into and as @Nathan Emmert has wisely pointed out how their funds are going to be used.

Do you think it's wise to hypothetically save up a large down payment while also waiting for interest rates to decrease in order to make the move into a house-hack?

This approach can often be beneficial in negotiations with the sellers too  As an appraiser, I can tell you it's not wise to trust the assessed value.

I think timing wise 2 makes sense for the election too.

A wise investor will not try to get rich quick with shortcuts.

A wise investor will not try to get rich quick with shortcuts.