In the summer months,  I prepare for the new students arriving for the semester. 

Be prepared to negotiate and walk away from unfavorable terms.

They may have been looking left and preparing for a 12%, 15%, 17% return and never paid attention to the risks on the right.  

I’m preparing for my retirement by getting into real estate 

If the water would have came back bad we were prepared to replace the pipe but was told this repair would be around $8K. 

I'd share that if I did, I'd be prepared to pay them to vacate.

You just buy as many as you can and then figure it out, there is no way to prepare, you just deal with it.

How can I best prepare for managing two rental properties, including handling maintenance, vacancies, and tenants?

As a former planning commissioner the people AGAINST projects are the loudest so you want to make sure you have a good pulse on what your neighbors and the louder people at public hearings stand so you can be prepared ahead of time. 

Without reserves, they might be unable to evict tenants or prepare the units once they are vacant.