The more experience earned, you gain insight into comparables, learn neighborhoods, get better and better in determining a real deal from a stinker.Sounds like you earned a little break now!

You can't easily determine whom has paid and who hasn't.  

@Trevor McCormick to piggyback off what others have said, determine if you are trying to maximize it as an investment or utilize it as a vacation home you will STR to help cover expenses, as this could dictate which type of property you are looking for. 

To determine what to offer on a rental property:Determine reasonable market rent, NOT the highest!

@Geoff Engel depending on what amount of available cash you are starting with and what you ultimately want to achieve will help determine your path.

Financing is important but your realtor will absolutely be the determining factor whether you purchase correctly or not. 

Lenders usually determine whether properties are lendable based on the debt service coverage ratio. 

Keep learning and determine your long term goals.

Determining whether to do a cost segregation study or not has a lot variables.

Quote from @Benjamin Ying: @Michael Smythe I'm new here, how do you determine property class if you're looking on Zillow?