It simply made sense from an opportunity cost perspective.

If so, from a tax perspective, when is that income realized... when the deposit is made (or transferred) or when the security deposit account is closed out when the lease expires/tenant leaves?

While its difficult to adopt this perspective while making money selling homes and closing mortgages, we're headed down an ill-advised path.Since the government can continue to print money, defer the ever-increasing debt, and add burden to the productive through direct and indirect taxation, it has no true (short term) economic accountability.

Do I benefit from tax perspective on any of these expenses I have to put behind the investment property?

Even after reading all the good books, and participating in these forums, this is a dynamic "game" -- and that's something that keeps this business fresh and exciting.BTW - I'm glad to hear your focus is "buy and hold" as I'm a huge proponent of it as a true wealth builder and I tell that to my investor clients all the time.Again, welcome sir.Continued success!

If you're calling up your perspective landlord, and all I can hear is kids screaming and yelling in the background, I'm probably not going to pursue that one, and I have kids too!

I strongly recommend Dave Ramsey's "Total Money Makeover" to give you a different perspective on this choice.

Pretend you are renting from yourself - you say you're paying that much now anyway, so paying that makes you cash-flow neutral from that perspective; at some future point, I assume you'll be having somebody else in there, so you'll get a rent payment then.Then when you analyze it, the cash-flow from the other 2 units will be what you can count on so long as you contribute your portion too.

You might be surprised of the limitations placed on you as a licensed professional related to collecting commissions on distress sales.My perspective is that of a listing agent, working primarily for banks.

Somewhat a feature, somewhat a disadvantage, depending on your perspective.