Needing Guidance For First Property/House-Hack

[Wyatt Nauman]

Hi BP! Here's my situation: 

My family has about $250-$300K that we recently acquired through a relative unfortunately passing away. We want to put a good chunk of that to use via real estate investing, so I will be house hacking a small multifamily or perhaps a single family with zoning for an ADU.

Thinking the Denver / Boulder / nearby areas because I would love to live around there, have lots of friends around that area - including my real estate agent who I'm good friends with, and its an appreciating market. 

My family and I currently live in a small podunk town in Iowa, which I truly can't wait to move from, and we rarely come across money like this (we're basically as middle as middle-class can get). My parents are putting me in charge of the entire investing process because they're too far retired to want to deal with it, so naturally I want to make sure I'm making the best decision for all of us. 

Cash flow is hard to come by in the Boulder / Denver markets and although the extra monthly cash flow would be great, and there's plenty of places in Iowa that will cash flow, I'm wanting to scale quickly and feel Colorado would be a decent place for that. 

To get a solid foundation for myself I'd like to buy at least 1 property to house hack in Colorado each year with a 5% down payment for the next 2-3 years. After that I plan to focus more on cash-flowing markets out of state. 

So, do you have any advice for a first-time house-hacker wishing to jump into the appreciating deep end and swim with the sharks? 
Is it more advantageous for me to do this in Colorado? Or should I stay in Iowa and aim at buying cheaper cash-flowing properties?

Appreciate any guidance! Thank you BP Fam!!!