This reminds me of the story of a wall-street banker convincing a fisherman who already has time for his friends / family to instead scale his fisherman business(get employees, integrate, then sell the business) all of which will lead him to be able to spend time with his friends and family.It already sounds like you have a great life - spending time wth family and in great health.Having additional money doesn't sounds like it would improve your life that much.

I would like if you ever need a licensed GC to do renovations/Tenant Improvement projects I have a group for that.  

In my experience, a successful BRRRR typically comes down to two main things: finding a good deal and managing an efficient renovation.

IT DOES NOT WORK at improving your financial balance at all.

Market Analysis: Palm Desert seems seasonal, so the cash flow challenge might not improve significantly without some adjustments.

You want to be able to demonstrate that your intent in purchasing, subdividing, and improving was to hold for investment use. 

Here's the key components to calculate your tax liabilityAdjusted cost basis - Is the purchase price, plus capital improvements, minus depreciation.

Net Sale - Is the contract price, minus the closing costs and commissions.Adjust cost basis - Is the purchase price, plus capital improvements, minus depreciation.

And how can we align our approach to meet those expectations and improve our chances of securing financing?  

Over time, rents may increase, improving your cash flow, and you’ll gain equity and valuable experience managing tenants and property operations.