Hi Joshua - what side of town are you going to work on? Are you a handy person capable of doing work yourself on a flip/BRRR deal? At a high level, the market here is a strong sellers market and folks doing flips/BRRRs here successfully have existing contractor relationships in place or do a lot of the work themselves since contractors are really expensive and in short supply and even then are having their margins squeezed by the high buyer demand. That said, there's a shortage of housing so as far as house hacking, a roommate situation may be your best bet to offset your mortgage costs initially until you get your feet on the ground and have a better feel for the area but even buying a single family house is highly competitive so you could always plan to rent one year to start doing more research to give you more time to find the best deal. I've lived in Dane County my whole life so happy to chat with you about specific areas you're considering, give you a feel for what things cost, etc. and connect you with lenders, realtors, etc.