The flood insurance has also been extremely unpredictable at any of these beaches, so that's a bit of a curve ball.

Since I’m holding these properties for the long term (30-year loans), I’ll have fully paid-off assets around the same time I’d traditionally start withdrawing from my 401(k).

You can open a Self-Directed IRA and use the IRA funds to buy a house using a Non-recourse loan. 

Went on to purchase additional rentals so tenants can pay down the loan and I build equity How did you find this deal and how did you negotiate it?

Prices are still low compared to most markets homes are going for around $204K on average but they’re steadily climbing.

the rest of the loan payment right now is coming back to you eventually. 

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

Also consider all lenders will require to review your insurance when underwriting a loan and it's likely a violation of your existing loan documents to let the properties go uninsured even if they didn't require insurance escrows. 

I would get the insurance in my trust name.

Is it hard money loans, angel investors, etc?