I’m also considering advising my tenant to look into Section 8 assistance, as it could help support their financial situation while allowing me to adjust the rent closer to market levels.

The tenants are currently in court with a title dispute so the house would have to be paid for cash only.I would like to convert it to a primary residence and turn the garden level into a separate two bedroom apartment for use as an in law suite.

If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

Whoever created the trust should be able to help you with that.

When analyzing a market and breaking it down into property Class submarkets, do you find it helpful to complete this division at the city-wide market level, or do you find it also beneficial to additionally break it down by suburb, and even neighborhood?

Following the shiny object, throwing money at a market you don't know well, and blindly trusting strangers that have a clear profit motive put you in a poor position to succeed regardless of where you choose to invest.

Quote from @Lolo Druff: I've heard horror stories about awful property management companies and am looking for a REFERRAL for a trusted source from an investor.

Congratulations on earning your broker license and taking your real estate journey to the next level!

Yes, trust me I know!

Fannie/Freddie both allow up to 90% financing. https://singlefamily.fanniemae.com/media/20786/displayHOWEVER, the  loan level pricing adjustments are HUGE on these loans: So, the rate and costs will be very high.