This is where your focus should be, not buying section 8 rentals or focusing solely on increasing your portfolio by 2x, 3x etc.

Yeap, exactly same as Zillow's Zestimate increased the price of houses.

I’m looking to ensure I structure things correctly and attract the right partners.

(Previous rent was $1,300 but we're about to put in a brand new kitchen from the studs, new flooring throughout the house, new furance, adding A/C, etc).So do we just pay for it all upfront and mostly drain all of our savings, or do I let the rent pay for it and utilize our other savings to get a second property this spring/summer to increase our cashflow? 

If you can rent 3 units for $2,000 you are close to breakeven.On the plus side, you will have a highly attractive asset and several decades without much cost of capex and repairs. 

Hopefully kept good records of improvements / anything to increase the basis2.

The property has a 3 car garage that could be rented to tenants to increase ROI. 

You would have to be significantly cheaper than my current cleaners for me to give you a shot, because I generally have only changed cleaners for either consistent subpar work or increasing/unreasonable prices.

Other most common factor: Family Size increases due to marriage or having a child. 

Increase your earnings, reduce expenses, save up, and invest.