I personally will try to avoid buying a home under 1000 square feet again.

It will be even harder as a young person with no life experience, and particularly no experience buying real estate. 

If the IRS has a Form 1098, they assume that the person listed on the form made the payments, and they move on. 

I personally do not have experience managing rentals.

Any insights or personal experiences would be greatly appreciated!

I spent many years managing myself and personally collecting rent checks. 

- 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.

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

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.

Id personally classify those as three different investing areas.