Healthy stable job market with jobs for all income levels. 

And by retired I mean making no income.

Under normal circumstances if you have more than 20% greater than cash to close in an investment or retirement account you will not need to show liquidation.

Do you think it is easier to retire with 2 paid off properties?

I am not opposed to obtaining another property to meet the requirements of said 1031-no true "obstacle" as I have good credit and a stable job. 

Mixing money and family is a recipe for disaster, particularly when that money is supposed to be for your retirement.

@Tamar HermesI use my retirement funds to invest in notes.

Even in trying times like these, an apartment deal purchased well is a stable asset.

My goal with this is to have it be a part of my retirement (I don't necessarily expect it to make me much now), and hopefully it will allow me to retire or partially retire a little early as well when the mortgages start to get paid off.  

I am a total newbie to investment properties, so please bear with me.I am considering purchasing a house in Gulf Shores/Orange Beach area initially as a vacation home and potentially as a retirement (way down the road) home.Before I ask my questions, let me give some information: I do not expect the home to be used by me, or my family, for more than 6 NON-consecutive weeks out of the year.