so you have three choices:
(1) buy a non-owner occupied property and rent it out (you'll continue living where you are now or somewhere else)
(2) buy a multi-fam and live in one unit, rent out the other(s)
(3) buy an owner occupied (OO) property and rent out a bedroom
do the math on each - with an OO you may qualify for an FHA insured mortgage which should allow for a reduced down payment (perhaps as low as 5%, sometimes lower). In addition, as an OO, your rate should be slightly lower than non-OO.
I believe an FHA loan requires you occupy the property for at least 12 months. while you need to double check this, if accurate, it means at month 13 you could buy another place, FHA insured at 5% down, and pick up a second property. that is a strategy you could implement over a number of years if the math works.
as for a multi-fam that allows you occupy one unit, vs. single fam house or even condo, it just comes down to math. there is nothing wrong with having a friend or random occupant rent a bedroom from you, as long as the rent reflects fair market value (so I don't agree that charging a friend rent "could strain the relationship" - unless you're over charging of course). beyond all that, it is absolutely critical, obviously, that you screen your tenant / roommate rigorously - and living with "friends" isn't always a good idea.
create an excel spreadsheet of these three verticals, any others I may have missed, with math predicated on what your local market reflects and feedback from lenders and see what it looks like.
