God wants us to depend upon Him solely for everything in life, whether it be for comfort or just about anything else. He wants to be everything to us and that is why we are commanded to love Him with all our heart, soul, mind, and spirit. So, don't feel bad for asking for money. "Ask and ye shall receive..." Matt. 7:7. The Lord wants you to tell Him your needs and He understands the storm that you're going through. I would also recommend reading about the storm that Jesus went through with the disciples, where He accused them of having such little faith and when He calmed the storm. I am not God and therefore, I couldn't tell you exactly the reason for all of the hardship in your life. Perhaps it is to test your faith and to better prepare you so that you can follow God more fully and to increase your faith. Your faith is sometimes all you have to hold on to. Just remember the verse in Psalms that No believe is left begging bread. I know that you have said you've been homeless, but the Lord will find a way to provide for you. Just keep praying to Him, seek His guidance and there will be a way.

Be strong in the Lord.
Sincerely,

Lost Love