I would gamble it all, spend it on more toys than I can afford, give away to ungrateful friends, and be happy forever....

I'd probably be gambling on appreciation, refi after a decrease in interest rates, or forced appreciation / rent increase via doing a rehab the first year. 

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).

But its definitely a gamble Ps also in RI.

I have a pretty upscale relatively new (4 years) gas range in my own home and you can turn the knob past the ignition point and just let gas flow on right into the home.

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.

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.