I am planning to sell a contiguous group of commercial properties consisting of retail, office, residential and land in an urban setting.

.- Once you have your criteria and you know what you are looking for, analyze deals every day until you can immediately spot a deal when you see one (and when you do jump on it immediately, there is no time for waiting around on today's market)- Keep taking daily consistent action and always showing up and that will get you to where you eventually want to go. 

Cost of hiring it out: All the above posts seem consistent in the market.

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.

The ECOA (Equal Credit Opportunity Act) states that lenders cannot disallow certain types of income such as pensions, alimony and public assistance, when determining the income of a loan applicant.A pension is a reasonably reliable consistent income source.

How would you keep multiplying your $$$??

Worth area I am consistently seeing 17 days on market for a rental before it is under lease.

How much new construction is planned for the area over the next few years,Potential for continued annual rent growth of 4% to 3% over the med to long term current local market conditions and prospects,Condo conversion potential given this property consists of only 2 and 3 bedroom units, ranging from 900SF to 1600SF.How much substitution threat there is (would potential renters rather buy a condo/townhouse) given rents range from $1,400/mth to $1,900/month plus RUBS and other extras?

i took a practice test till I was consistently passing( 3 times ) and signed up. 

At that point it just comes down to consistent marketing and playing the numbers game.I think an argument can be made both ways on coaching, I've used business coaches in the past and I still use what I learned from them.