Maybe you could compromise by finding a property that you can live in comfortably but also has rental potential (like a duplex).

As you keep learning, you'll get more comfortable with the numbers and figure out which strategy works best for you both.

When you are investor friendly it means you understand the metrics of the buyers property search.I have seen so many agents get comfortable and simply add their new buyers to the "Hot Sheet" and they blast the buyers with properties that do not even fit the buyers cash flow needs or budget.

It’s crucial for me to achieve a favorable appraisal, as my estimates place me comfortably below 80% loan-to-value.

It really comes down to what you are comfortable with.

Change it to "only buy deals that will comfortably yield X% return".  

Ultimately, Lawton could be appealing to cash-flow-focused investors comfortable with high-risk, high-reward environments and looking to leverage a reliable rental base tied to Fort Sill.

If you can show / prove to him that the park will be worth more because you are rebuilding the bathhouse, paving the roads and adding a playground then maybe he will feel more comfortable? 

Get out of your comfort zone.

I've only experienced this on the buy-side of multifamily acquisitions, but have been involved in transactions where the lender requires a CofO and they have gotten comfortable with just the I-card, when there is no CofO for the property.