Multi Family vs Vacation Rental? Regrets?

[Lauren L.]

I am struggling to determine my path! We have some money to invest and I don’t know what I am doing. HELP.

My #1 life goal is to leave my current job and be able to add another little one to our family next year and not go back to work. I would like to only work part time during tax season (I am a CPA).

My #2 life goal is to have a waterfront property in the Adirondacks NY that we can rent out in the ski season and enjoy in the summer.

My #3 life goal is to not be miserable.

I cannot decide if multi family properties is the right thing for me or if I should go the vacation rental route. I really love the idea of fixing up a vacation property for my family and others to enjoy! But, I’ve been reading so much about the benefits of multiple doors and multi family properties at building long term wealth and now I’m under contract on a multi family property in Schenectady Ny, a place like everyone says not to invest in. I am not actually excited about owning a multi family, and am doing it for the monthly cash flow (which may turn out to be minimal bc of some issues with the property and if that’s the case I will back out of course).

All that said, does anyone have regrets going one route vs the other route? I would really appreciate the discussion about your experiences!

Thank you!