It'll take time but can really pay off if you stick with it.I'm in Los Angeles and I've investing in TN and GA in the past, and currently investing in SE Wisconsin (your area).Let's connect and discuss the market.

You wont pay capital gains when you sell the house as long as it is in the SDIRA but you will have to pay normal income tax when you withdraw cash from the SDIRA after retirement but would you rather pay income tax on $90K or $300K?

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

If you’re interested in investing in real estate, you can consider doing so with a Self-Directed IRA to defer taxes on capital gains until you actually withdraw the funds from your IRA.

If my business owner bank statements did not gain me an approval, I was going to go the hard money route.

Figure out the state and federal capital gains tax and depreciation recapture after selling costs.

The biggest gains come from going all-in on one market and really getting to know it inside and out.

Rental income is subject to tax, but it is also possible to deduct many costs related to owning and maintaining rental property, including property management fees, repairs, and mortgage interest payments.Additionally, for those investors holding properties in Germany for the long-term, the country's capital gains tax law is attractive.

Quote from @Shaun Ortiz: Hi Jason,Thanks for sharing your journey—it sounds like you’ve gained some invaluable insights from your experiences, even with the squirrel tenants (that’s definitely a story!).

After two years your only profit will be the education you gained.