In your post, it seems you've tried to address @Dave Toelkes point by saying that the training will enhance your skill set for your current position.The upshot of all this is that much of what your proposing falls into areas in which many taxpayers take many liberties, but regarding which you may want to get advice from a tax advisor that knows your overall financial and tax profile.You mention formation of an LLC as a component of your tax strategy.

I actually love my job.Bigger Pockets is such a great site/service/community/lifestyle and I truly feel privileged to call myself a member.Thank you for reading!

I have a tenant that is willing to pay for significant upgrades that will greatly enhance my property value. 

It may not hurt to have a chat with them, but don't expect them to change their lifestyle.

I'd imagine I could achieve the lifestyle I want much earlier if I were to focus on cash flow rather than liquid assets.My question is, if the goal is to get to a passive cash flow of $10,000/mo, what's a realistic amount of money to have saved up to accomplish this?  

This is not something I would ever recommend until you are on the ladder and have made some money and are comfortable if the decision does not go in your favor but I believe this is the next step in an investors career path to grow and enhance your portfolio.Are others venturing outside their comfort zone and if so what has been a success for you and why and when did you decide to venture away?

They would have to have major change in their life style in order to do so, and most will not or can not do that!

I could live right now off my disability and school money without making any cuts in my lifestyle.

Bass really carries, so no bass enhancement devices either.Since your sub-floor is attached directly to the joists without the sound control between them the noise will carry a lot from above to below and from below to above.

(A good lifestyle without having to worry about the grass and shrubs or any upkeep).The management is typically very professional and the apartments can be as spacious and upscale as your bank account allows.Good Luck!