Hey @Gunnar Conrado, great to hear you are getting into RE investing, and in Madison. It's an awesome market for appreciation, but cash flow is hard to come across unless you put more than 20% down. If you house hack of course you can take advantage of included rent. If house hacking, find a multi-unit rather than a single family and renting rooms out, then you can separate utilities and have more privacy. Also, consider if you will be going into a deal looking to use FHA (3.5%/5%) downpayments. In Madison, you will be competing with 20% or all-cash buyers, especially for the first-day-on-market HGTV remodeled homes. I'd edit the search to 30+ days on market, sellers are usually more apt to work with more conditions FHA require. If you're looking to AirBnB the other unit look into Dane County codes & Madison regulations, I believe Madison has some length-of-stay regulations. It can cash-flow you more and will always work in Madison, especially downtown area.
There's a number of steps you should consider prior: What's your max budget?First, Get qualified on lending (bank/credit union), THEN find a realtor - (Ale Broz at Keller Williams, Madison has helped me buy and sell multiple properties last two years), then you can go into offers strong with a pre-approval with the help of a professional realtor. Any realtor will ask you to get preapproved before making offers.
If you need help on market specific rents/values DM me and we can discuss specific addresses, I have 100+ BP Calc/deal apps analyzed Madison, WI Properties.
Hope any of this helps,
Good luck out there!
-Angelo