Been reading a lot and it does seem like the numbers regarding cash flow for a single family home on Maui (right now) wouldn’t work too well.I understand and accept that passive income is for the people who’ve built a massive net and are at the top (but even then I think they have to work and make sure their system stays functioning)I really want to learn more about owning/operating vacation rentals, specifically in HI if possible and specifically the tax part of it (now with the shift of the 2018 tax laws).I’m going to dive through the forums and try find more books on the topic.

@Isha  do you have a specific niche that you target or are you just looking to cash a check?

Do you have anything in your lease that specifically holds them accountable for plumbing clogs?

But I digress- it sounds like you haven't identified specific buying criteria for yourself.

@Jason BocekCongratulations on your successful start in investing.To correctly create a tax return, you will need to learn a few concepts that are specific to REI.

Hey @Stephen Swanson,I am also moving to back to Florida (Naples specifically) and will be doing the house hacking idea as well.

Hey BP,I've been thinking recently on a topic that surprised me when I realized I had kind of thought this way my whole life and that is - going across the river to Illinois.To be more specific, I grew up in O'Fallon.

And like I said earlier I only to door knock very specific people. 

But that doesn't mean you are discriminating and it doesn't mean you would be found guilty.You are offering a reward to a specific group of people that are not a protected class.

They are going to give you the best advice that will work specifically with your strategy and your goals.