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.

Is there anything you actually need to do for this type of conversion?

Even just entering the listings or vacancies might get you very conversant in the local market.Then you could also make some key contacts, learn the process, and maybe even find your first deal (a client may be willing to owner finance a rental, for example).If you are handy, you might try and work with a firm that does apartment turnovers (make ready) or even as a laborer for a remodeling contractor (especially one that does flip work for others or on their own)--to get the full hands on view of how to get apartments ready to rent or flips ready to sell.Maybe the best hands on way to work in the space is to buy your first rental; maybe your first or next home could be a duplex or single family with an accessory apt.Best of Luck.