If you weren't using Quicken, I would also recommend having separate asset accounts (and accumulated depreciation accounts) for every class of depreciable property.

Then they went on rent, lack of cash/equity accumulating, bad cycles.As long as you're in the military and getting HOA.

I'm earning interest on these investments and it's starting to add up, but I'm not making money on the interest income that is accumulating. 

> You don't get to write off your negative gains until you sell the property (they accumulate each year) or have a positive year to balance against. 

Much like a private lender worked very hard to earn and accumulate his/her cash in the bank that he/she loans out. 

The overall goal is long term wealth accumulation. 

I am not even going to go into mangement problems, tenant drama, domestic and violet crimes, vacancies and rent collection issues..I have seen the backend of the story as well, because I am getting calls from out of state investors, who have accumulated small portfolios of these low end properties and when they start they are loosing money after a few years they want to liquidate the portfolio which is not that easy. 

If you are in expanding (or wealth accumulation ) phase, it is rarely a good idea to pay fees(or points) for lower rate. 

It's a trophy, that is worth accumulating, but can be lost just as quickly as it was found because it is based on the economy and the specific property values of that market. 

If you decide that accumulation is in the cards, it never feels like a bad time to clear $30k from a cash-out refinance AND lock in a fantastic interest rate for the next few decades.