That being said, I fortunately have the means to close on two properties and I'm wondering whether it makes more sense to maximize my income and real estate purchasing qualifications (e.g. consistent employment, income, etc.) now versus trying to acquire my second property whilst in a new career with less income.

I explained that my goal was to acquire 1 property a year (through loans) for the next 5 years while I still had a W-2 to help prepare for retirement.After he put together our fin plan, he advised me that I should hold off on these properties and instead concentrate on putting more money into my 401K (currently only putting 5%, no employer match) and to pay down the existing loans for two of my other properties.

I also have a 457 b that I can withdraw as soon as I separate from my employer.

They’ll jump right in with you as a partner if you’re a 1st time homebuyer crying the blues over detached home prices. ..because of course everyone employed 36.5hr/week or more should be able to afford a detached 3 bed 2.5 bath (usually new build) house no more than 15 minutes from downtown in all major cities...

Unemployment: ideally, % is decreasing over last 5 yearsPopulation: 5-year population growth is increasingPopulation age: 5-year population age range of your target demographic is increasing Industry: ideally, no one industry is employing more than 25% to 30% of the employed populationTop employers: look up the top companies, determine what industry they are in, and calculate if that is a growing or declining industrySupply and DemandIs the supply of your product (SFRs or multifamily) increasing?

The Metroplex proper has mostly tech and other professional type employers plus a bit of heavy industry and defense contractors. 

Not because of discrimination but by the luck of the draw because I run credit reports and verify employment.

Welcome to self employment. 

As long as you meet the credit requirements, have the 3 percent down paymentand have steady employment, you will likely be approved.

Judgment needs to be employed, having to go to court to patrician a property or force sale is costly and takes time, but with the proper agreements you'll be in the driver's seat.