Astra,
This is a great way to express your goals and get some motivation from the folks on this board. It should be an interesting year!
I live on the east coast, so I can't provide any advice on routing for you. However, I have two suggestions, one of which was already mentioned. In light of your aggressive schedule, I would seriously consider an accelerated IFR program that can get you the ticket in about 10 days. It is gruesome and tiring work, but worth it in terms of efficiency and time. I did mine through PIC. Since you will be flying frequently, you will not forget that which you have learned quickly. It will become second nature. If you were not flying often I might discourage you from doing that. But, as Seth and others have said, getting your IFR should be your number one aviation priority.
Second, if you are going to be regularly flying single pilot IFR, you need a good working autopilot. Period. Since you are doing some cheaper radios upgrades soon, that is great, but if you don't have an autopilot already I would seriously consider investing in one. It can be a life saver.
Finally, I live near Seth in the DC area, so let us know if you get around this area sometime and we can get together.
Good luck.
Fernando
PS - I would not mind trying to get my commercial ticket this year either. Hmmm.