My initial strategy is likely to buy a 2-family that needs work with 25% down using hard money loan to fund the purchase + rehab, get it stabilized/optimized and rented perhaps to section 8 tenants since I like the idea of that guaranteed rent/ seems to offer higher revenue than true market rents (I have been a real estate agent for over 10 years and am aware of the risks/rewards/diligence needed to succeed with section 8 tenants and have worked with many landlords with section 8 tenants but am new to investing myself), then re-finance at a higher appraised value back into a more standard loan while keeping 25% equity into the deal.

I agree with you that RE in unlikely to be your optimal path.

A slightly lower CoCR in a market you understand well can outperform a “better” deal you can’t actively manage.For first investments, proximity often matters more than optimization.

Full-system assumptions, an unknowns premium, and anchoring to low comps all force the deal to work under stress instead of optimism.

I can only base my optimism of breaking even on the information and data supplied, let alone the follow up by Versity. 

The debt can derail the deal later on when debt service rises or a call in the market forces a sale at a non-optimal time.

No, but I do sometimes wonder what I am leaving on the table that I could be optimizing better.2.

The key is understanding the full menu of financing options upfront so you can choose the right tool for the deal instead of paying unnecessary points simply because you didn’t know another option existed.

And what are you using to help optimize the SEO? 

Unless you are holding cash for a planned purchase or attempting to mitigate SORR heavy in CDs is likely not optimal for long term growth.