Have You Ever Gone "All-In?

[Derek Luttrell]

I am 25 years old and, thanks to excelling at my commission-based job since graduating 3 years ago, I've been able to save at a pretty solid rate. I own and am house-hacking my primary residence in Chicago, and am pre-approved on another $100k investment property with 25% down at 4.75% with a minimum loan amount of $50k. 

To get down to numbers, I have $30k in savings, $20k in personal stocks I've been toying with since 2016, a few grand in crypto for the heck of it, an IRA, and 401k that I put 10% of every paycheck into that I would never withdraw from (company contributes 1.5% on top of that).

I'm heading to Indiana this weekend to look at some $20-30k SFRs that need around $10k of TLC, and also some duplexes in the $60-100k range. I love the idea of owning something outright off the bat, but it would essentially deplete my current liquid cash savings--has anyone gone through something like this before? If I go the financing route, my initial investment (25% down) would be less skin the game, which feels more comforting, but I would also lose cash flow to the lender. I'm pretty stuck on which is the better move for my first jump in the water. 

Thanks for reading, 

- Derek