Am I getting greedy to ask for an additional seller credit at closing to help offset some of repairs needed?

A low LTV refi to get you some additional cash should be enough to clear this up.

million in addition to their investors (who expect a reasonable rate of return) by keeping the rental rates at a fraction of the market rate?

Additionally, I was not making enough from my corporate job to support any kind of significant mortgage payment.

Does anyone know of a calculator where I can plug in the additional yearly pay down along with the appreciation rate of my area? 

These are professionals with additional training and a stricter code of ethics.

Thanks for any additional input you have time to put forth. 

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

Any details you can provide would be helpful.Since I have the next 12 months to plan for this, I am open to any additional feedback/suggestions on what else I should think about.

Some carriers won't allow insured to be a trust, so in that case do it in your company name with trust as additional insured.