For podcasts, BiggerPockets has great episodes on house hacking—definitely worth a listen!

This is not tax or legal advice, just what I personally do, consult your professionals! 

However, as I walk down the street in my city, I see tons of retail businesses that definitely do not comply. 

And agents are legally prohibited to engage after closing - at least per Wisconsin State law. 

Isn't it unlikely that a homeowner who cant afford a 2-3k tax bill would even challenge this legally?

I have been part of a regular meetup for a couple years now and it definitely helps ground you in your local market.

Has anyone had any luck obtaining legal counsel and fighting this?  

You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

I'll definitely check out Set For Life by Scott Trench and The Total Money Makeover by Dave Ramsey for more financial insights.Watching BiggerPockets podcasts and networking with local investors are great suggestions.

But be mindful of the debt service requirements and ensure your rental income is sufficient to cover the loan payments.It’s definitely possible to scale up with DSCR loans—many investors use them to build large rental portfolios.