If you opted to go this route, I'd recommend a lengthy conversation with at least one, or ideally a few people who have done this before.

Having these conversations with the CPA as I converted my books has completely changed the way I think about my record keeping, how I take draws, how I may structure partnerships and investors going forward....Other than perhaps a good real estate lawyer, from my experience, a good CPA is critical to a young real estate investor's performance. 

Then when you get out (if you get out, if you are doing a career this is a different conversation) you take your raft of money and start house-hacking. 

I am a new investor myself with a whopping 1 deal under my belt, so I'm not sure I am the best advice, but I would say the absolute first step is to have a real in depth conversation with you bride to know what's comfortable.From a monetary perspective, I would buy a cheap home in a good area that needs many repairs, add your sweat equity, and trade up your home in 2 years (or re-finance and use that to start earlier).

Zoning issues with the City are a major concern - - frequently, SFRs in an R1 zone prohibit such conversions, and if you proceed regardless, will run into issues when/if you sell the property.B+ for thinking out of the box, D- for unintended consequences.

This will allow the questions and conversations to come out naturally.

Buying a building that supports owning a second home that I share with another investor is lifestyle hacking more than anything.I was writing this to start a conversation to speak about how much harder it is for others getting started must be having house hacking.

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But just having this conversation is very helpful to me as I try to plan the next 5-7 years.

I look forward to future conversations, and I am sure I will be able to use all the help and knowledge I can get.