House Hacked a 3-flat in 22, Questions for HH #2

[Jake Kinney]

Hello Chicago BP Community,

Back in 2021, I came on the Chicago forum and received some phenomenal input and contacts that led me to my first house hack in 2022. I have a feeling Brie Schmidt might see this, so thanks again for the incredible amount of help during that purchase and my beginning as an investor.

Quick background: I work in tech (remote job) with a good W-2 income and have lived in the northside of Chicago for 17 years. I'm very familiar with the north and northwest side. With Brie's help, I closed on my first house hack in April 2022 in west Logan Square (near Scofflaw, just north of the 606), putting 10% down and got a 30 year fixed at 4.125%. The property has a large 2-flat main building (3 fully finished floors and partially finished attic) and a large 5 BR coach house. I've had to do some work to the property (drain tile in basements, insurance claim for plumbing issue) but I knew that things like this would happen and I could stomach these expenses with my W-2 income. I moved out of Unit 1 last August to move into another rental unit closer to my fiancee's office. Things are going smooth at the property with all 3 units rented out and a comfortable amount of cash flow each month.

I'm anxious for house hack #2 next year and I have some questions I'd greatly appreciate some feedback on. 

1. Best areas for long term buy and hold? I've heard many times that moving NW from Logan Square into Avondale and Portage Park is a pretty foolproof approach. My fiancee has to commute to the loop, which is an important factor. 

2. How have financing options changed since 2022? I am aware of the 5% down programs available. 

3. Sense check on the rents of my units: 5 BR 3 bath coach house with 1 parking spot ($2,500), 5 BR 2 bath duplex down ($2,450), 3 BR + den 1 bath unit with brand new kitchen, plus parking spot ($1,450). I know the 3 BR unit is under market but he's a long time tenant and does a lot of work for me. 

4. How can I scale my portfolio faster? This is the number one question on my mind. I have a decent amount in retirement accounts but I'm not sure if it's a smart move to leverage those. I can continually save up enough for another down payment through my W-2 income, but the time elapsed kind of drives me nuts. 

Thanks in advance for your time and input!

Jake

[Jonathan Klemm]

Hi @Jake Kinney - Great to see you jumping back into the forums.  You are surely one of many Chicago investors @Brie Schmidt has assisted on their real estate journey, Brie is great!  

Love that you are ready and hunting for your next deal!

1.  I love all those neighborhoods you mentioned NW along the blue line - you can't go wrong long-term

2. FHA 203k and homestyle (5% down) are amazing financing options. If you can do the renovation, the deal will get even better!

4. If you have switched jobs and your retirement is in an IRA vs. 401k, maybe consider rolling it into a self-directed account to invest in other people's deals with that money (aka private money lender, syndications, etc.)