I've read there are a plethora of obstacles I could face even if I'm the winning bidder, I'm just not exactly sure what those are or how they might occur.

If we file again and not taking the money, are we definitely will win ?

I can practically guarantee that painting them would be cheaper in the amount of time you spend on the matter, even if you win the case and get reimbursed for attorney's fees, which is not guaranteed.

Wins for both of us.

I know the expenses are more as well but you can definitely win in that market.

You have 20k in equity sitting there at X rate, if you can pull that out and make greater then X rate including closing costs on your new loan then its a WIN situation.

I kept a record of the winning bids and was wondering if I should contact these owners myself (for the larger amounts) and let them know for a small fee.  

For office I recommend, How to Win in Commercial Real Estate Investing.

However, depending on which entity is looking at you, doing so could be construed as circumventing the law (and proving otherwise could be a costly lesson, even if you win).The moral of the story... when there's a licensing issue, proceed with caution and err on the side of licensing (as you have already pointed out).  

Could be a very good win win situation.