I use Anytime Mailbox and it's been great. There are other options that are probably good as well. About the form, that's just for USPS purposes and I'm not a lawyer, but I don't think it creates any concerns for your liability protection. I don't think anonymity is a typical concern for most people, but as far as I know, it's not an issue for that either.

No, most people aren't exempt from taxes. And taxation isn't theft. We live in democracy where the majority of people prefer to live in a society where we have voted to require ourselves to pay taxes because the majority of us want schools, roads, national defense, and even support for seniors and free school lunches so kids at least don't go hungry. It's not a perfect system. There is plenty of waste, and we all have different ideas about who should pay more or less in taxes and how the money should be spent. But is taxation in general theft? No, it's what the society you are apart of has chosen because most of us prefer this to the alternative options.

Yeah, you basically have the option to either market as "goods and services", or send the 1099-NEC (if you pay them over $600, or now $2000 starting in 2026). Personally, I don't check the box for goods and services so they get the full amount, and I send the 1099 (it costs something like $1 or so with TaxBandits).

There can be legitimate reasons why you can't expense expenses that occur before a property is placed in service or rental. It's complicated, but by default, expenses before it's placed in service are usually added to the cost basis of the property by default. But there are exceptions, such as items that can be depreciated over a shorter class life. And there is an election you can make to expense startup costs for certain kinds of expenses (at least up to $5k, and the rest has to be amortized). I'm not a bookkeeper, but $3,000 may be reasonable depending on what all is involved and how many transactions. There's probably more work involved in what they would do than you're thinking there would be. Since you mentioned things like a chart of accounts and classes, I'm guessing this is using QuickBooks. In general, I don't recommend using QuickBooks for rental properties because it does tend to end up easily becoming a complicated mess. For accounting for rental properties, your life is so much easier if you use software designed for that. Stessa is very good, but actually Baselane is my new favorite one to use. With simpler software, there's usually no need for a bookkeeper. Bookkeeping for a rental is super simple. It's just putting expenses into categories like utilities, repairs, etc. It's just QuickBooks that makes it complicated, and then a bookkeeper is needed.

@Xerxes Clayton I see. Something like Mint or Monarch is probably also just fine as long as they can categorize your transactions into categories that make sense for a rental, especially if they let you setup custom categories. You generally can't just deduct expenses before the property is placed in service, even if they're under $2,500. You can elect to deduct them as startup expenses (section 195 of the tax code). But that can't include property taxes or loan interest (those amounts should be added to the cost basis of the property that is depreciated). And the startup expenses can only be deducted up to $5,000, and then the rest has to be amortized over 15 years. But realistically, most tax pros don't know to do that, and most will just include the startup costs as part of the property depreciation. But if you have over $5,000 in those types of startup costs that you just deducted as an expense, that's not allowed.

If your LLCs are single-member LLCs and not something else like a partnership, the tax law doesn't care what LLC pays for expenses, the LLC is just a disregarded entity for tax purposes. It might make some difference on a human level if a particular IRS agent in an audit is swayed by seeing an expense on an LLC's bank account rather than your personal account. But technically it doesn't really matter. As far as deducting that as a rental expense, that type of thing can be a legitimate rental expense, yes. I was reading a tax court case a little while back where that type of expense was disallowed, but that was just because in that situation the taxpayer didn't actually have any rental properties yet. Education expenses to go into a new line of business aren't deductible as an expense, but education can be a legitimate expense for an existing business. By the way, some of these mastermind and network opportunity real estate course things are legitimate, but the vast majority of them are scams or borderline scams. I hear of so many people who wasted money on real estate education and network schemes. From the ones I hear about, it seems like the ones that cost a few hundred dollars and are mostly educational are probably legit. The ones where they have fees going up into the thousands of dollars tend to be scams, and the ones that cost tens of thousands are scams seemingly 100% of the time. (And ones that involve any kind of investment partnership with the people offering it, or if they provide the lending or sell you the properties, etc, that's a big red flag.) How they price what they are offering tends to reveal whether their focus is on providing education or making themselves rich. And if they start using heavy handed sales tactics like telling you not to not worry about the price and instead focus on how much value it can bring to you, etc., just run. In most cities, there are local real estate mastermind meetup groups that are usually completely free and really are a great resource to learn from other investors.