I know hiring a CPA or advisor is a good idea at any point, but at what point in an investor's progression does it become a necessity?

I work with agents because of their expertise in their markets, and yes a little help in analysis but you must establishes your habitat as an investor. 

If you want to be in it for the long haul, start establishing those relationships now so you create repeat business and a strong referral network. 

You need two years of established income in a commission based vocation to qualify the income for pre-approval, so my generous uncle graciously co-signed for us on the loan.

It might stop the bleeding for a bit but it could lead to worse consequences down the road, I'd advise sitting with a CPA/tax advisor with all information and finding a strategy that fits your goals. 

They also have the right to screen potential tenants and establish their own rules and regulations, such as pet policies and late fees.

I do have a fairly extensive background related to personal finance with teaching Personal Finance and previously having a career as a Financial Advisor, but as for REI I am hoping to make my first multi-family unit purchase in the next 6 months.  

Would you benefit greater from establishing a new connection with another lender/broker partner who can possibly give you another lead in your area in the future2.

I’ll likely spend a few weeks down that way early Jan to better understand the local market, neighborhoods, and establish a network.

Establish a relationship with an Interior Designer as I offer a consultation and by the hour or Negotiate a day rate.