@Joe Lambert,If your net passive loss is too large for you right now, don't stop taking a depreciation deduciton, but instead,refuse to claim active participation in your rentals. 

After an initial discussion with him, he came back to me and told me investors he works with have started lending money to house flippers and have stopped flipping themselves.

After exploring the 70% LTV option at 20 years, it turns out you need 2 years of established rents in your LLC to qualify or $250k in an accessible account (non-retirement). 

She replied saying, "I know how to access the county's site."

First, don't be too hard on yourselves, but this one line in your initial post is what investors have to stop saying."

I think the lack of vehicular access means there’s a whole chunk of the market that is taken out, which would be the wealthier vacation home types that don’t want to deal with getting on and off the island.

Stop taking money out of your own pocket to be considered an "investor". 

Good luck, don’t rush it, open a Roth with no fees to at least have one in case they are stop having them as well as starting the ownership clock. 

If you stop by or call Tom Noonan 742-8200, he can either give you the names of reputable contractors, or turn you over to another of his salespeople to help you out.

Unless you have the ability to access the property pre-foreclosure, you are effectively buying sight unseen at the auction.