We’re thinking through a few different options:- Moving out of our current house and making it a long-term rental, knowing that we could get about $1K/month in cash flow-Purchasing a house in either northern WI, or a dream location like the mountains of MT/NC/TN/WY that we could fix up and live in for 12 months, eventually converting to a STR (we’d like to take a gamble and live somewhere adventurous before kids, but settle down long term here in WI).

HSBC can help you get checking accounts setup in almost any country.We are taxed on our world wide income in the US, but that’s not that big of deal, as we have treaties with other counties to help avoid double tax, and you can always setup up IBC in Cook Island, or St Kitts & Nevis, thus off shoring the income earned outside of the US, if you bring it home you will have to pay taxes on it.

But its definitely a gamble Ps also in RI.

You're basically gambling on the property a) not depreciating or losing value in the between your purchase and refinance and b) leaving A LOT up to chance with the appraised value coming in higher than your debt outstanding, and doing so with a significant enough of a margin where you're either not coming to the closing table with cash or cashing-out.

Furthermore, since we don't plan to live in this place long term, any chance of enjoying the benefits of refinancing when rates drop eventually are also a gamble.

If you really really want it, then accept 250.Remember, the other side is also gambling.

The best one is to put each property into a separate land trust, with the beneficiary being a multi-member LLC, consisting of an offshore C-corporation general partner and a minimum of 10 revocable trusts as limited partners - per property.

Appreciation is always a gamble - the past will not necessarily look like the future (especially in California).

It could appreciate but I consider that gambling.

Sometimes you have hot years and others are a bit slower.Each decision is a gamble…a risk you take based on the best information you’ve gathered from research and wise counsel.