I have no experience personally investing with them.   

I would spend money to enhance and update to current standards the search functionality and person to person tagging so it's easier to find stuff.

Ask your employer if you can have your pay split up into three deposits, one to investments savings, one to your checking account for personal use on a daily basis, and one to an emergency account you can tap into so you don't have to tap into your investment savings.

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

I personally believe that a better way to jump into mid term rentals is to take a course on buidling a property management company or cohosting business where you bring your skillset to the table without the intial investment into all the furniture and leases.

I dont know Nathan personally..

For my own personal goal reasons, I am going to still with searching for a lender who will be open to it.

- Loss of historical data (for both IRS audits and for personal portfolio tracking.)You should be able to print the general ledger and Balance sheet / income statement for each period.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

Any insights or personal experiences would be greatly appreciated!