Starting Out – Western WI - STR vs Multi-Family vs BRRRR

[Matt Haselwander]

Hi All – I’m looking to get started in Real Estate but like many, am not sure where to focus my time an energy. Unfortunately suffering from “analysis paralysis” by constantly reading real estate books, attending webinars and listening to podcasts but not taking any action.

My fiancé and I currently live in a 4-bedroom, 2 full bathroom house in WI that I purchased with almost 2.5 years ago when interest rates around 3%. I’ve stuck about $20K in improvements into the house and now am estimating roughly $150K in equity that I’d like to roll into my next investment. We’re thinking through a few different options:

1. - Moving out of our current house and making it a long-term rental, knowing that we could get about $1K/month in cash flow
2. -Purchasing a house in either northern WI, or a dream location like the mountains of MT/NC/TN/WY that we could fix up and live in for 12 months, eventually converting to a STR (we'd like to take a gamble and live somewhere adventurous before kids, but settle down long term here in WI). Obviously we'd have to do some research on local ordinances, STR market, etc. before making that decision
3. -Network locally to find off-market multi-family or apartment complexes to purchase, fix, and rent out. We’d either live in one of the units so that our mortgage is being paid for, or, stay in our current house while still investing
4. -Build or remodel a boutique STR in Northern WI where we could charge a higher price point and manage ourselves part-time if needed. (My fiancé would prefer this route given her social media knowledge and talent – confident that we could create a destination location that generates bookings year round)

Additionally, I have a solid W-2 income (>$175K) that I’m using as my foundation to fuel new investment opportunities. I don’t intend on giving up this position any time soon but also know that it’s taking my time and attention away from truly building up passive income investments.

Any guidance (or networking opportunities) would be much appreciated.