We'd love to hear any success stories of people house-hacking into financial freedom!

Your brokers going to need to have a good financial incentive to hang your license with them.

Again I would not have had this before investing in real estate.Also, his desire for liquidity may just make you change your strategy to buying single family since there is the largest market of buyers for that type of property, and at least right now in my area everything is so hot if i wanted to sell I doubt it would take more than 30 days to sell a property and liquidate my money.But he may not know these things or see how they will effect y'alls financial situation.

I also use Google drive, so all of the property documents, rehab plan, invoices, etc. are accessible for the investors to view and a spreadsheet on google drive with the property financials and weekly updates. 

if you didn't file then you can still do so.Lenders want at list 2 years financials and credit score. you could possibly House Hack a small multi family 2-4 units on very good first home buyers terms, which are often with very low down payment. 

They have no legal obligation to compromise on the assessed amount, as far as I know.

At the same time, IL/Cook is not doing good financially, so I'm sure it'll just go up.Declining population is a concern also.

I just want to achieve financial independence from this business in the long term. 

I’ve seen a number of deals where a Roth buys an option on a “financial friend’s” rehab for $1,000.

If it's been longer than 7 years, you might just leave 'em.I recommend Dave Ramsey's Total Money Makeover to get your financial house in order.