Buying A Property to Rent While Still Renting Yourself

[Joseph T.]

I've been interested in buying a smaller multi-family property to live in and rent out the remaining unit(s). I'm having trouble finding something in my area that analyzes appropriately as a "good deal" unless I include the rent for the unit I'd be occupying myself in the income ("paying myself"). So my questions are:

1) When acting as an owner/occupant, should you include the rent of the personally occupied unit in your projected income when analyzing the property? Or should a truly good deal cash flow positively AND include you living for free?

2) Since obviously single family homes outnumber multi-families, I'm considering expanding my search there too. The only issue is I rent an apartment now myself. No complaints with where I'm living now but is it silly to be a renter when you're also a landlord yourself? I suppose though if you're generating cash flow from the rental and building equity in it too but still paying rent for your own living, it's still not a bad situation. 

What do you think? Hopefully expressed my questions clearly enough. Thank you in advance!