I understand being a very cautious person. No doubt he is a perfectionist and wants everything to be just right and in order before you two marry. The only problem is that there is no such thing as a perfect time and no such thing as perfect order. It is like the old saying, "If you wait for all the lights to turn green, you will be waiting forever." Here is an example: he could get everything in order, with himself and everything else. He could get a great job, you could get a nice place to live and have a nice wedding, nice honeymoon, etc. The next week he could be out of a job. You see, there are no guarantees in this life. The only thing we can rest on is our future with Christ, but other than that anything can happen. Tell him to remember this....GOD IS IN CONTROL!!!! God loves marriage (He created it),and He also promises to provide for us. Remember that there is no such thing as perfection. Marriage aren't perfect,lol.
I hope this helps in some way. I am a very cautious/worried person myself. However, my wife and I met and married in 8 months. This is was very uncharacteristic for both of us, but it is the best choice we have ever made.
"God has not given a spirit of fear, but of power,love, and of sound mind"...(somewhere in one of the Timothy books)
Again, hope this helps