Take a house that sold at a low price twice in the past.  

@Tanner KingWhen I analyze a house hack deal, I focus on metrics like GRM, Cap Rate, Cash Flow, House Hack Savings, and Future Rent Potential.

What do you do when in house goes on vacation? 

Also if you are selling, hopefully your agent has advised you but good practice to have a vacant unit to open the buyer pool to owner-occupied buyers/house hackers.

This is basically a math problem that will depend on both you personal finances & also how much of this is an investment vs you want a nice house to live in4.

It was the worst house in the best location. 5 acres just above a lake outside of a desired town.

What is the average acquisition cost of the houses?

Happy to discuss this further on what might make the most sense for your end goal.If you are renting right now and starting your path in real estate investing, as said above, I really do like the house hacking strategy for your situation.

Maybe just try that and explain that you need some credible house to tie them to.

Once you land on the right PM, transition everything to them.As others have stated, four houses is not a big task.