I’m wondering what type of information I should prepare to present to this person as well as general tips for approaching a private investor.

Otherwise you can either try to find some local wholesalers or flippers (go to any local REIA meetings or other types of Investor meet ups), try selling it outright or simply find an agent willing to list it for you.

It's a relationship type business played on a local field.Take inventory of you strengths and interests.

People from the around the world want to invest here (especially in multi-family), and inventory is extremely low across all types of real estate, especially single family homes. 

Since you're going to live in the property, I would keep your property search focus to the type of house you'd like to live.  

I personally do not like portfolio type deals because investors tend to over value the assets based on a cap rate, when the reality is that single families and small multis should be sold based on comps. 

Note: I am aware of online applications like cozy that makes sure they fill out and pay their background/credit check but the applications for those types of software doesn't cover everything I want to ask and Brandon suggested paper applications is the way to go so it being my first rental I'll follow his advice on that but I just need a robust way of doing it.3.

I focus mainly on fix and flip type deals, but do a small amount of wholesaling also in addition to some new construction and buy and hold.

Has anyone tried such a strategy, or know if there are people who are interested in purchasing these types of properties? 

@Terri David you could possibly "hire" someone, for reduced rent, to look over the property and do showings, meet with contractors, etc... on a smaller building, but you'd still need someone to manage payments, marketing, tenant screening, etc.... it could save you some money on the management side, but you still need some type of management company, if you didnt want to do it yourself