I just joined the Montgomery, AL Investors Club and hope to get over to one of their meetings in the near future.

For future reference, birds of a feather flock together.

However, this generic statement is useless for many reasons:- your two years are never identical- even if you expect them to be identical, we don't know the future, and things can change- you likely have a number of special factors that change your tax outcome, some of which I mentioned above and others mentioned in earlier comments on this threadWe are also assuming that you're selling outright for cash and not reinvesting, although you have other options such as installment sales (aka owner financing), reinvesting into REITs/DSTs, opportunity zone funds and more, as mentioned in other comments.Finally, nobody brought up what I consider the single most important factor in your decision process: you sell when you have a good offer, period.

This requires an income that rises faster than inflation, or you will not have the additional dollars you will need to pay future inflated prices.What causes rents (and prices) to increase?

Currently I have utilities figured out and have met with the city planner and my future plans after annexation follows their vision of the comprehensive plan for that property but he passed me off to the county since I’m not annexed currently and the county wants to pass me back to the city.

We're planning a virtual meet up in the near future. 

I’m looking at a similar strategy as you, starting with a small investment first — but I’m eyeing a larger investment in the future for sure. 

It makes sense to rent and save up that extra money to apply towards a future purchase. 

If ever that you'll need help funding for your future investments, I’d be happy to review any project and see which program would be the best fit.

Far from covering your negative cash flow but covers half of it and is a good indicator of future rent growth.2.5 years ago i purchased my first negative cash flow property (but for years i claimed I would buy a negative cash flow RE if my underwriting showed a return that met my criteria) and it was a lot more than $800/month negative with my underwriting (which was quite close to 50% rule).