The cash flow from multi family is a nice way of supplementing your income over time.  

Now that I'm in the top tax bracket, there's a 20% tax rate difference between long-term capitals gains (20% + a 4% Obamacare supplemental tax) and short-term gains (39.6% + the same Obamacare tax).

Last year I purchased 3 condos under my name, a few months later I put all my condos into an irrevocable trust I was already charged supplemental taxes as a new owner now I am getting charged supplemental taxes again as a new owner because it is set up as an irrevocable trust under my name is that correct?

I am looking to produce a positive cash flow that will supplement my military retirement and VA disability.

I'm also looking to supplement our retirement with a passive income of $3000-$3500 a month.

Are you just looking to supplement your income with one property?

Lost the client to a technicality, make sure you check with the homeowners to see if they didn't have a list like Eddie mentioned or sign a supplemental reinstatement with the listing contract.

I am an IT professional and I am just looking to supplement my current income as well as prepare for retirement.  

For example, if it was hearing about how someone had supplemented their retirement by building their real estate portfolio through Buy & Holds, then you should look into learning more of that.

Your intention in getting a vacation home also needs to be to use it for your own use and the rentals are supplemental.