Buy and Hold. Deciding weather to hold or sell.

[Matt Honeyford]

Hello, I've been wrestling with a decision for the past week and I'm looking for some advice. 

We are cashing out of a flip, which we are currently living in, and using the profits to put 20% down on our 'forever home'. 

Here's what I'm struggling with: We also have a buy and hold on Park Avenue in Rochester NY. Which is a very desirable neighborhood. Currently it cash flows about $500 per month, but with the addition of a 2nd full bath i feel it could cash flow at almost $800 (which is what comps are renting for). It needs a paint job and a new roof. I'm considering selling it and paying off our current forever home. So what's better; no mortgage on a primary home and no investment property -or- mortgage payment on primary home and investment income?

[Naftali Freedman]

I would say mortgage payment + investment income.

Here are my thoughts:

1. Tax benefits for mortgages

2. Low interest rates, lock the mortgage now

3. You can always sell the investment to pay off the mortgage

4. Value/income of investment can go up