New Investor in Madison, WI w/ 1 Deal Done, Looking for #2

[Andy LaVoy]

Hi All,

My name is Andy and I'm a relatively new investor in Madison, WI. 

I cut my teeth on my first purchase in 2017, a one mixed building with 2 commercial tenants and 2 residential tenants. I had an eviction in my second month of ownership, which cost me a good chunk of my reserve fund with legal fees and vacancy. It's now rented again and I'm in the process of rehabbing the upstairs warehouse space into 2 residential units. Also, I had a building heater go out in January which set me back a couple grand. This first project has been awfully difficult motivationally, but I feel the cruising point is near, and it should cash flow well at that point.

All that to say, I haven't given up but I'm thinking about my second investment. My background is in software, and that's how I plan on funding my projects. My goal is to build out a cash flowing portfolio that can replace my income, but I'm really struggling with what to take on next. There's a lot of advice about how to do a specific type of deal, but how do you pick which type of deal works for you? It seems like buying multi-unit residential is how many people start, so I guess that's where I'm at now. The Madison market is white hot, so I'm considering shopping in more rural areas around Dane County where I can get in at a lower price. I'm also considering buying some land in Mount Horeb and building a 6/8 unit apartment there. I'm not really sure how to go about financing a land buy + complete build, and I don't know how to find a contractor to do the architecture and build, but I'd love some advice on that. 

I'm considering getting my RE License for access to the MLS, to write my own contracts, and just to learn more in general about the industry. I also want to grow my network, I'd love to learn from other successful investors in the area. I'm a math nerd and love to run numbers, I really just don't know where to look for or how to apply the math across an entire industry (there are so many ways to go, something I love about REI is that creativity can win). I think I could be valuable to someone locally helping build out software for analyzing projects, I do have some of my own money to invest, and I'd be happy to do grunt work while I learn.

Happy to chat with anyone willing to give advice and I appreciate your time,

Andy