I don't think it's really that important to have the logo designed exactly the way you want it. The most important step is the 'word mark' or 'standard character mark' the name itself. You probably don't want to spend $300 for each class of good in the short-run, but minimally get the main one down, so you have some grounds to work from. The most important step is adding the TM to the name and logo being used in commerce. This helps protect the name ahead of time.

You can file the trademark yourself. I would look at all the competitors in the space through trademark searches, see how they define the trademark and the define your own balancing being really broad vs. very exact. If there is a problem in your filing, the attorney at the trademark office will help you out and you don't need to pay anything. They can't advise you on how to protect the name, but they will ensure the wording in form is correct. Actually, I was quite impressed at their customer service!

This is all just my opinion, I am no expert in trademarks. But I love the process of building a name brand. Trademarks are pretty important to avoid complications that you have encountered. Good Luck! Sorry for the woes and I hope you find a really cool name. Luckily .coms are loosing some ground as the ONLY name to get these days.