Sounds like you are on the right track! I just visited Portland in October - what a cool city! I think paying off debt is the first priority, however, it sounds like you will be able to do some things quickly if you are able to save $5,000 per month. I would start by making a list of all multifamily properties in the areas you are wanting to live. I have a program called rebogateway that can scrub data including all multifamily properties within an area, including high equity, out of state owners, title info., mortgage info., etc. I would try by sending yellow letters (starting by ones that have "for rent" signs or posted evictions - landlords do get tired) expressing an interest in the property and your desire to "house hack". I would try to put together an owner finance deal (or lease option if there is still a mortgage) with a small down payment and a 5-10 year balloon payment. I just purchased a duplex with owner financing and a 5 year balloon. It will cashflow extremely well those 5 years. Those deals are out there and if you are consistent you will find them. Good luck!