The way you allocate the proceeds doesn't matter. 

I allocate my time toward finding the next purchase and make my money on the purchase.

@Wen ChenNone of that is an expense.Costs specifically connected to obtaining the mortgage (appraisal, credit report, origination fee etc.) are combined into "loan costs" and then set up for amortization over the length of the mortgage.The rest is added to the purchase price and results in "tax basis" which is then set up for depreciation over 27.5 years, after allocating a portion of the basis to land.If this process sounds complicated (which it is) - you may need an accountant to help.

This is not to mention allocating the bills, going after the tenants is a total PITA.

Also, I am unsure how to handle the escrow payment as the payments are never allocated to P/I vs.

Generally a REIT might buy a large portfolio and not want all of the properties to re-balance their asset allocation percentages of a certain tenant type or asset class.

If you do flips, that would save taxes, but flips are better conducted via S-corp and there is no way to specially allocate income high earner. 

However, without going into details, I would recommend breaking down the expenses to make sure you have allocated all the expense needed such as management fees (even if you do the management yourself), cap ex, vacancy factors, etc... 

I agree completely as an investment strategy, owning 1 property means 100% of all expenses are allocated to one home and that can be problematic.

@Andrew Dodds, the way I read what Amber and Chris wrote, you could treat your $181k remaining VA entitlement as if it was a HELOC (like having existing equity), which should more than cover the required deposit that you might need for your next $500k home.Of course, your Non-VA Lender will go through your Debt-To-Income Ratio with a fine tooth comb, so depending on how much Rent they allow you to allocate towards your income, you could be good to go!