Help me see if my strategy to jump into RE is sound or crazy

[Asya Anderson]

I've been reading so much great info here on Bigger Pockets -- So first of all, thank you! 

I'm looking to get started in buy and hold investing, SFH and/or small multifamily. I'm currently renting in a HCOL area (Southern CA) so my initial thought was to buy a relatively turnkey SFH with decent cashflow in a cheaper market. Keep it simple and have a property manager, etc. just to do something "easy" to get my feet wet for my first deal. However, my wife and I very much want to move out of state, ideally ASAP for all kinds of reasons I won't get in to here. My wife plans to go back to grad school next fall (2019) and we don't know where we will may need to move for that, but we really want to get out of California before then.

My current thinking is this: Buy a small multifamily in a LCOL area and house hack/BRRR it between now and Aug 2019. It would require me to quit my job, which is terrifying, but I was planning to find a new job in 8-10 months anyway. I'd plan to get some kind of job in the new place, but we would probably move without something lined up for either of us and focus on getting the rehab started.

I'm thinking of purchasing a 2-4 family B/C+ neighborhood building for ~$150K in Cleveland, Minneapolis, or a similar market--still looking for exactly the right place. (And the numbers have to work, of course). 20% down, live in one unit while rehabbing the other(s). Rent out the units (probably with a property mgr) as they are finished. Refi and pull out my $30k+rehab $, Move to new place for wife's grad school (and maybe do it again). Long term goal would be several buy and hold units that cash flow well. 

Questions:

How hard is it going to be to get approved for a loan if I leave my job? If we do this as cheaply as above, I have assets (currently invested in an investment account, but easy to liquidate) that could cover the balance of the mortgage if necessary. I would probably pull some of these funds out for the rehab. However, I'm assuming that without documented ongoing income it might still be hard to get approved? (This is literally my first mortgage so no idea here). Alternatively I could get the loan while still employed in CA and plan for 25% down and categorize it as an investment, but then I'm paying more interest than I want to out of the gate, especially when I do plan to live in it, at least at first.

Is this a crazy plan? I am really digging the idea of getting out of my 9-5 for a few months and going all-in. But I have zero experience with real estate or rehabbing anything and few/no connections in the markets where we are looking. I am concerned I could easily get in way over my head and maybe my original take-it-slow approach would be more prudent...

I'd love advice on the above plan, or alternate ideas that would get me where I want to be. Thanks!

[Ali Boone]

Okay, whoa. Got a little dizzy reading this for a second.

It seems like to me you had a good plan nailed in the first paragraph with just buying a steady property that you don't need to put work into using your W2 paycheck and income to support it. But then you started thinking of everything....backwards....ish.

Quit your jobs, then go invest in a rehab house-hack project in a random town, then wonder where you'll get jobs and/or move, all while you have no experience doing any of that. The backwards part of this is- no, you won't get financing with no job income, but more crucial is- what happens if your house-hack/BRRRR/rehab thing goes bust? You quite honestly say you've never done any of thatkind of stuff before and don't even have contacts in markets, so that screams super-high risk level to me, and you want to do that with no income coming in from anywhere else?

It's not that any of your plan is undoable, but you've got to be smart about it too. Rehabs and house-hacks don't always work out as planned, so how do you cover and protect yourself just in case? If you have no jobs, you can get no loans, so how do you do that? What about nest eggs?

I'd say the things you want to do are great, and you can absolutely do them, but maybe rework the steps and order of the steps in order to do it... a little more gracefully?