What to do with personal investment transactions that I don’t want to transfer to Brokerage account?

Question

I make various personal investments in real estate throughout the year. These investments come from a ‘Detailed View’ Brokerage account so I am able to catalog the transactions as needed. I find the current requirement of transferring these investment transactions to a custom Brokerage account and then 'buying' shares unnecessarily complex and frustrating.

If I don’t want to create a custom Brokerage account to transfer these investment transactions to and then buy shares, is marking the Brokerage investment transaction as simply a “Transfer” the best option? I don’t want the transaction to show up as an expense either.

hbwilliams22 · Answer

"I make real estate investments as a passive limited partner through a real estate investment firm. "

It comes from cash within an Detailed Quicken Brokerage account, yes.

Tom Young · Answer

"I make real estate investments as a passive limited partner through a real estate investment firm. "
This is some sort of Account in your Quicken file, presumably an Investment Account?
"All transactions both outflows and inflows happen from a linked checking account. "
Why a "linked" checking Account?  Is this a real-world account?  Typically I'd expect the cash you invest and the distributions (income, proceeds from sales?) could settle into the Quicken Investment Account.
"What I am toying around with is creating a custom "LLC - Investments" Brokerage account and transferring the checking account outflows and inflows to this account when they happen. "
Than makes sense to me.
"For distribution transactions, I am not quite sure what to do. For example, when the first $20,000 deposit is made to my checking, if I transfer this to the "LLC - Investments" Brokerage account, it shows as -$20,000."
If it's settling directly into your checking Account, that's the place, normally, where you'd do your accounting.  If you somehow want to have it flow through your LLC - Investments Brokerage Account, then create a dummy $20,000 in the Investment Account, do your accounting for that $20,000 in there, then "transfer" the $20,000 from that Account.  That creates the "-$20,000" you're referring to, offset by the dummy deposit of $20,000, leaving the cash unchanged.
"Instead of transferring transactions back and forth, is there a better way? Ideally, I would not have to bother with buying and selling shares as these are simply real estate investment transactions and not the buying and selling of stocks. "
You certainly could do this by simple "Asset" Accounts instead of "Investment" Accounts.  The accounting would be exactly the same either way, except for the Buy and Sell aspect, and the Accounts would simply show up on a different place in your Balance Sheet.  
If the firm you're dealing with provides periodic estimates of the value of your various (I assume) real estate holdings, then using an Investment Account pseudo security makes a certain amount of sense as you can update the "securities'" quote, see how your various properties are doing and have a closer accounting of your net worth.  Too, you don't absolutely have to have securities in an Investment Account.  If you want the real estate investments to be shown on your balance sheet as investments but don't want to see the investments' values, simply run the cash back and forth in those Investment Accounts, with no securities involved.

hbwilliams22 · Answer

@jacobs @Tom Young I make real estate investments as a passive limited partner through a real estate investment firm. There are multiple investment and distribution transactions throughout the lifetime of the investment. All transactions both outflows and inflows happen from a linked checking account. For example:

Investment #1: -$10,000
 Investment #2: -$10,000
 Investment #3: -$10,000
 Distribution #1: $20,000
 Distribution #2: $20,000
 Distribution #3: $20,000

What I am toying around with is creating a custom "LLC - Investments" Brokerage account and transferring the checking account outflows and inflows to this account when they happen.

For example, when I wire the first investment of $10,000 to the investment firm and it shows as -$10,000 in my checking account, I transfer this transaction to the "LLC - Investments" Brokerage account which puts a $10,000 balance. I then "Buy" 10,000 shares at $1.00/share which zeroes out the account. I will do this for each investment transaction that hits my checking account.

For distribution transactions, I am not quite sure what to do. For example, when the first $20,000 deposit is made to my checking, if I transfer this to the "LLC - Investments" Brokerage account, it shows as -$20,000.

Instead of transferring transactions back and forth, is there a better way? Ideally, I would not have to bother with buying and selling shares as these are simply real estate investment transactions and not the buying and selling of stocks.