Living in Las Vegas, we see gambling winnings and losses quite often in Chapter 13. If you continue to gamble, and you are lucky, the bankruptcy trustee will expect you to pay more to your creditors. If you continue to gamble and your luck is bad, you may not be able to afford to pay your Trustee and that would mean your Chapter 13 and all its benefits would be lost.
Answer Applies to: Nevada
The problems you mentioned should not, by themselves, keep you from getting a discharge in Ch. 13. But because there are some problems, I strongly suggest you find a lawyer experienced in bankruptcy issues to advise and represent you. It's almost always worth the investment.
Answer Applies to: Wisconsin
Answer Applies to: Michigan
You need to see local counsel before you do anything else.
Answer Applies to: California
The gambling losses will not be a problem as long as you can say you have stopped.
Answer Applies to: Oregon
No but trustee may monitor future tax returns and if continue to gamble may be problem.
Answer Applies to: Florida
Gambling will not be a problem in filing a Chapter 13. From your description, you might be able to strip the second mortgage.
Answer Applies to: Ohio