Newbie - house hacking + long term strategy help

[Remon Rasho]

Hello All,

I've been on this forum (on and off) for years and never quite made anything work in Real Estate as I didn't have the income or credit to invest. I sold my property a couple of years ago and moved from IL. to CO and I'd love to stay in CO., but the houses I've seen are so poorly managed that the delayed maintenance costs coupled with the higher priced market lead me to believe no property in CO. is worth picking up.   

My goal was to "house hack" a duplex, living on one side while renting out the other. The goal was to get out from renting, and to charge enough rent for one of the sides that my housing costs would be limited/as close to $0 as possible; however, I just can't find a property that would allow for that. Even if I were to eventually leave, the two sides typically can't be rented out to cover the mortgage, taxes, etc... 

So I'm looking back at IL. Specifically the NW suburbs (McHenry County Area + Parts of WI.). I would be getting a loan/pre-approved for $330,000 and I've found a few properties in IL that seem to make sense, but I just can't tell if I'm calculating rents properly or anything like that.

My ask:

I think IL makes the most sense as I know the area; however, there has to be better states and suburbs to look at for long-term cash flow. Could anyone help me make sense of all of this? 

Year one -> I would like to house-hack my first property and possibly buy a second cash-flowing property (depending on the downpayment required) 

Year two plus(+) -> I would like to continue purchasing one or two properties per year with the goal of leveraging enough income that I can leave my job and invest full-time. 

I just don't see a clear path to doing so and I am feeling a bit stuck. 

I would greatly appreciate any light that could be shed on this situation. I am open to suggestions and criticism.

Luckily I work remotely (and so does my wife) and we can virtually go anywhere.. just not looking for high-crime areas where we'll get shot, mugged, or worse lol. 

Thanks for checking out my post. Have a blessed day!

[Paul De Luca]

@Remon Rasho

To get better cash flow, you should ideally target a 3-4 unit property to house hack and eventually move out of. I'm not sure what opportunities are available in WI but a quick glance at the MLS shows multiple 2-3 units available within your budget.

Sure, there could be "better" states and suburbs for long term cash flow. To me "better" in that sense means lower cost of living, lower property taxes, and less expensive properties. But if the property values and taxes are lower, then it's likely that the rents will be lower as well. And maybe the tenant base isn't as good. 

There's a bunch of markets across the midwest or south that could be better for long term cash flow, but if you don't know those markets then you're going to have to spend time researching each given market to make an informed decision on where to invest.

I think it's a big advantage that you already know IL. But if you want to explore other markets for opportunity, just be sure to do your homework.