@Cody Evans @Ana Garrido- My dad always taught me that "the lazy man works twice as hard."...that said, fully agree on needing the plan. I'm exploring options at the moment, so plans are still baking. My thought is that the more liquidity I can get my hands on, the better positioned I'll be to move when opportunities strike and leverage deals. My high level thought right now is to buy in cash, but with economics that would work had I taken out a mortgage. I want my cash flow to all go to new home purchases, until I'm out of money, then take the equity out of homes and start again. Location, property type, etc still has some factors that I'm exploring to see more of "when" I'd need to sell my primary. I can always dump my condo and get moving on some deals before then. As far as market pricing goes, I'm of the stance that I'd be selling at a bit of a premium right now, but who knows where the market will head. I have continuously been shocked by it, thought my primary should get hit pretty hard by the new tax bill for the next buyer.
@Raul R. - I'm from the Bay Area, she's from NYC. Part of this equation might mean moving to the East Coast, which might give me some negotiating power with her! So we'd technically be liquidating the house anyways. It'd be more about NOT buying a new house right out the gate while we figure out areas, rather than moving straight toward a rental in the same town. Outside of that, I convinced her it's taking a gamble on me overall, but that my track record professionally and personally justifies it. I have a family and I never would put them in jeopardy, and I have a career I wouldn't plan on altering unless something drastic changed. If we don't take a swing in the next year or two, I think the rest of our lives will be fairly predictable, and rolling the dice in an intelligent fashion to put a new trajectory on things sounds attractive to each of us.
