First, there are about 6 states that I refuse to invest in because of their tax laws and what I consider to be an unfriendly business environment.

Out of my 32 properties, I’ve seen insurance rates drop by up to 40% on renewals, and property tax increases are finally slowing down compared to the crazy jumps we saw over the last five years.

Appreciation: Are you primarily looking for immediate cash flow (rental income exceeding expenses) or are you betting on long-term appreciation?

All-In Costs & Profitability-ARV: $450K-Purchase Price (financed): $170K-Repairs: $150K-Holding Costs & Financing: ~$20K–$30K (insurance, taxes, utilities, interest, etc.)

Which made my tracking for taxes and such all look super dumb because everything is off by a dollar.

You must have the Business tax license & pay all the fees required.  

And for the evidence, I would guess that they'll want to see some evidence of the income from the rental days.

Even if you rent at a break even or slight loss, if you could have 3 years of rental income offsetting your mortgage while realizing 3-6% appreciation, could be worth it, especially if you think appreciating for this area will exceed national averages.

It should cash flow 400/month after taking taxes/HOA into account.

How much is your household income?