We have several qualified people who have already requested an employment application.

Also how long would I need to rent it out for to be considered applicable for an 1031? 

To be clear, it is totally ok to APPLY for more than one (shopping rates/lenders/brokers) however having multiple loans going at once (if you were doing a loan for your primary and one for a rental at the same time) requires disclosing on the application that you are getting another loan while your current loan is processing.  

When a vacancy comes up in a good apartment on SFO, operators often have literally hundreds of extremely well qualified applicants at incredible rates.

Keep in mind you cannot discriminate Section 8 applications. 

Since we don't have our primary yet, I feel like it doesn't make a ton of sense to get into buying rental properties and potentially hurting my own mortgage loan application.

This period of Short-TermRental Operation shall be specified by the property owner in the required LakeGeneva Short-Term Rental Application.

Here is some free advice (worth what you pay for it):Upon application, obtain a handwritten statement from the borrower describing the intended use of the money.

RentRedi and other similar services can help manage applications, leases, and maintenance requests in one place.

I am sure I will learn a lot of base knowledge but will not likely be applicable for Canada...