The broker indicated they had never dealt with a tax deed transaction and was at a loss as to what to tell the Underwriter.Has anyone encountered this issue, and if so, how was it resolved?

I am sorry to hear of your losses in the crash.  

After the rehab, we generally re-apply for a landlord policy and cancel the first one.A big part of this being reality is huge losses to the insurance companies where a so-called "investor" buys a property cheap, insures it, and then a short time later has a catastrophic loss and a large payout from the insurance.  

There really is no logical reason why the landlord should have to store the tenants items as opposed to getting rid of them or keeping them to try and recover losses that they incurred during the eviction process.

So suddenly your 17% "return" turns into a 20% loss.

Between the brawl with publisher Hachette over e-book prices, drones, and the Amazon Fire phone’s flop, losses are heading Amazon’s way."

My question is, do I need to change my tax strategy and not show a loss, or do I need to pay myself a wage? 

Asking him to never reply to another post of yours is rude and putting you at a loss by limiting yourself by not having the resource of Ben's advice.  

Everyone wants to fight for their slice of the loss to get as much as possible before releasing the lien interest.There are called "loan servicing guidelines" that a servicer has to follow.

Based on those two data points there is no deal.Understandably you are anxious to get in the game, and may have even jumped in without the resources of BP, but you cannot work the property and risk the loss of capital, for the reward of $20/month.