Two LLCs, one for Appointment Reminder and one for everything else. The separation is exactly because AR has potentially high liability in event of a HIPAA incident and, while I'm insured against it, I don't want DHS to have a claim on substantially all of my business assets in the event that everything goes wrong.
I go back and forth on whether I want to take investment at some point. At the moment, mostly working on other things, but who knows what the future holds.
I do not want to make assumptions, but because your concerns are regarding potential liability (and rightfully so)if those are single member LLCs (you are the sole owner), then you will not be receiving the limited liability legal protection generally associated with the LLC.
AFAICT, generally (and, of course, as this is mostly a state law question, there will be variations in details from state to state), the single member of a Single Member LLC (SMLLC) receives the same protection from liability as those of a multi-member LLC (or shareholders of a corporation), but in many states an SMLLC is not as protected from liability for the personal debts of its single member as is the case with a multi-member LLC.
Single member LLCs may be more likely to have defective LLC operating agreements (apparently, a common error is to use a template agreement designed for a multi-member LLC) or be more prone to having the owner engage in the kind of behavior that would permit piercing the corporate veil, but that's not the same thing as the SMLLC form not having the same protection as other LLCs.
EDIT: Just to reiterate a point others have made in this thread, if you are making a decision on this for a business you plan to run, do consult an attorney knowledgeable in the laws of the jurisdiction you plan to operate in. Big picture discussions may give you an idea of the landscape and the concerns you need to be aware of, but you don't want to find out too late that a critical detail wasn't covered, and a couple paragraphs on HN aren't going to cover all (or, likely, even a sizable fraction) of the salient details of business law relevant to your circumstance.
You bring up a very nuanced point regarding the direction of liability for single member LLC.
As you state, it is correct the owner will generally be protected from the liabilities of the LLC. With the exception of piercing the corporate veil, alter ego doctrine, ect...
However, single member LLC can be liable for the debts of the sole owner. Meaning the business assets can be attached, charging orders issued and ownership can even be foreclosed. To distinguish if I own stock in say Google or Apple, and I am in a car accident and kill someone and I can't pay a judgement obviously the judgment holder can not collect against Apple/Google even though I am an owner; however, they could collect against an LLC I own if it is single member. Alternatively, if the same LLC was multi-member generally the judgment holder could not satisfy the judgment against the multi-member LLC.
Edit: In fairness, Patio11 expressed concerned about the liability from his LLC flowing to him personally. Nevertheless, I always feel it is relevant to consider personal liability flowing to the LLC.
Generally, charging orders can be issued against any LLC for a member's debts (all a charging order does is require that the LLC pay any distributions that would go to the member to the creditor instead; a charging order to an LLC for a members debt is similar to an attachment order to an employer for an employees debt.)
In some jurisdictions, though, single member LLCs, unlike multimember LLCs, do not restrict creditors of the member to these kind of actions against the member's financial interest in the LLC, and allow the member's creditors to seek direct payment from the LLC as if it owed the debt.
(Also, in some states, charging orders aren't the exclusive remedy for members debts against multimember LLCs, either, which one reason you need to know the law of the jurisdiction you plan to operate in.)
Just to be clear about this subthread between 'will_brown and 'dragonwriter:
They are talking about the reverse of the case most people think about when they think about corporate liability protection. Specifically, they're talking about the way the law handles the case where your personal liabilities spill over into your company's liabilities.
For example: if, unrelated to your work, you hit someone with your car and end up losing a $100k lawsuit, your victim will investigate attaching that liability to your equity in your company. With C and S corporations, this isn't complicated: an attorney pursuing a collection can take your shares to satisfy the liability. This is possible because C and S corporations have mostly straightforward rules for transferable stock ownership.
But due to a quirk in the law, LLCs don't. LLCs are glorified partnerships; they are a way of getting most of the benefits of a corporate form with much less of the pain of forming an actual corporation. As a result, there is no straightforward way for a court to transfer partial ownership of the LLC to a creditor; to do so would be to impact all the other LLC members, who did not agree to partner with the debt collector.
The obvious result of this quirk is that people form LLCs to protect personal assets from collection. An attorney pursuing a collection can attach themselves in some ways to the beneficial interest in the LLC, but they cannot get any decisionmaking power for the LLC, and they cannot get transferable stock in the LLC (which stock doesn't exist). So, as long as the LLC never issues a distribution, the assets housed in it can potentially be judgement-proof.
Since this is a loophole for debtors big enough to drive a truck through, some states have legal precedent that gives special consideration to single-member LLCs to make them easier to collect against, since the whole rationale for them being difficult to collect against is the protection of other innocent partners, which don't exist in an SMLLC.
why would that be, as long as you don't co-mingle personal funds with business funds and otherwise treat it as a legitimate, independent and separate business, I don't understand how you could be held liable. http://en.wikipedia.org/wiki/Piercing_the_corporate_veil
Google "asset protection of single member LLC" to find a trove of scholarly/legal articles on the subject, add your State for State specific explanation.
Basically, the LLC derives its existence from "partnership laws", just as it sounds partnerships entail two or more owners. As a result, the majority (if not all) States have case law on point where the Courts do not extend asset protection where there is only 1 owner of the LLC.
Here is the Florida Supreme Court Case on point, but I am certain you will find a similar case in most other jurisdictions, and if you do not find a case from your state, more likely than not it is because they did not hear a similar case yet (LLCs have only been existed in the US since 1977, and States slowly adopted the concept over time), not because they have case law going the other direction: http://assetprotectionworld.com/wp-content/uploads/2012/06/O...
I go back and forth on whether I want to take investment at some point. At the moment, mostly working on other things, but who knows what the future holds.