It drives me crazy when I hear these stories preventive maintenance is what should be practiced and discussing all avenues of the deal and the borrowers docs in advance.   

What type of interview do you do with existing tenant(s) to ask them about maintenance issues?

There are books written about this details but keep you focus on the end goal.The first deal turns theory into actual tenants, actual maintenance problems, etc. 

However, there are lenders who offer more flexible terms or even no prepayment penalties, depending on the deal structure and your investment strategy.To find such lenders, here are some options to consider:No Prepayment Penalty Loans: Some lenders, often private or portfolio-based, offer DSCR loans without prepayment penalties, though the trade-off might be a slightly higher interest rate or fees.Yield Maintenance or Defeasance Alternatives: Ask about other prepayment structures like yield maintenance, which can sometimes be less restrictive depending on market conditions.Custom Terms: There are lenders (like us at Phoenix Funded) who can structure loans tailored to your needs.

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

Another thing that my brain keeps milling on is the fact that if in a normally purchased deal, I work hard and pay off a 3 million dollar building in 20 years, and then don't pay my 80k annual property tax, I'm going to lose my 3M building that I "own" but somehow don't really actually own.

I am not opposed to the idea but definitely need to get more educated on the details such as where exactly, is it too crowded of a space, how to be competitive, maintenance requirements for a beach rental, etc.

Speaking from the Arizona perspective, we are experiencing continued growth, attracting lots of new residents (Californians choose Texas and Arizona as their top 2 places to move).Here's an economic forecast:https://www.azcentral.com/story/money/business/economy/2019/12/11/arizona-state-university-annual-economic-forecast-predicts-slower-growth/4398074002/Not sure where you are getting your "low rent" thoughts, maybe compared to CA.

But it's also mildly higher maintenance. 

Usually, when I buy a duplex around that price range in Cleveland it's closer to $500 a unit annually or $1,000 a year.