The market is crazy right now and will be for the next 2 to 3 yearsdue to inflation devaluing the dollar, inflation increasing newbuilding costs.

Richmond certainly would have some potential in pulling trades from, but coming from Lexington, you might face an added trip charge on top of the service provided.Over the past few years, rents have increased nationwide.

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

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

(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? 

That way they keep their licenses and ratings.I don't see much of a difference really.Don't keep them out as they will get increasingly suspicious and they might pull your permit for non-compliance.

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

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.