I'm an EN user for only about a year or so and don't use it at any level remotely "close" to its potential. More importantly, though (and perhaps more relevant to this topic), I've been a health insurance broker for nearly 40 years. Most MD offices have systems that will "know" if - or which - of the office visit charges are considered "preventive" vs. diagnostic, etc. (the covered charges mandated by PPACA [Obamacare] are very specific) and will let you know this when you're "checking out" of the MD's office. ALL medical charges that are not preventive will fall under the plan deductible, so those should be relatively easy to keep track of. Remember, too, that you'll receive an "EOB" (Explanation of Benefits) from your health insurance company after every medical charge you have and it will show how much was covered, how much went against your plan deductible, and how much of your plan deductible you "satisfied" year-to-date. Finally, if you've also established a tax-sheltered HSA (health savings account) and put money into (a process that is separate and distinct from your insurance plan and premium) you'll most likely receive a debit card linked to that account which may be used - if you wish - to pay for those charges at the time of service (leaving the MD office, drug store, etc.) - with the funds in your HSA account. If you use the card, you'll receive another statement from the HSA account itself documenting the amount of the payment. This means you already have 2 sources of documentation: (1) the insurance plan's EOB each time a claim is filed, and (2) the HSA account statement (if you used it) showing the amount paid and to whom. How does EN fit into all this? Virtually any way you wish: copy (via scan/email or photo) of medical receipts, EOBs, HSA account statements, etc. for later, tax-filing purposes, or even input the dollar amounts manually; set up a checklist of your major health spending categories (MD; Rx; Lab & Xray; etc.) and "list" each one individually. I'm sure there are endless ways this could be done if you'd like to do so. I think EN is a fantastic program and I'm constantly searching for ways to further integrate into my working (insurance) and personal "systems." I'm hoping those who may be "further down" the implementation road will weigh in on this topic (and anything related to insurance agency, sales, & related uses for EN). Hope this helps a bit, though!