For example, my 2/1 would normally rent for $600 per month, but once furnished and fully converted, I rent each room for $2,200 per semester or $8,800 total for one year (not counting the summer months). 

Are the lender fees what they promised....for underwriting, processing, appraisal, etc.guaranteed rate is normally pretty good on fees, but there may be charges that are out of their control.  

I was able to get more than I would normally had I rented the entire unit out.

@Christopher Hardy @Jessica DilksIt depends - If your W-2 income has enough withholding to cover other forms of income where there is normally no withholding(Interest, dividends, Business income), then there is no need to make quarterly estimated tax payments.The issue is that the IRS does not to paid once when you file your return.

This also encourages people to delay, delay, delay maintenance until they sell their own condo, and so condos under this system usually go downhill.The other way is for the HOA fees to be high enough so that stuff like new roof, new parking paving, new siding, etc, can be financed and then is paid out of the normal fees. 

Educate yourself (due diligence), get a plan based off your schedule/lifestyle, and get after it.

The turnover itself required some cleaning they missed (under appliances, mopping, windows, cleaning carpets, etc), carpet replacement (normal wear and tear) and painting which I know I can't charge for, but were an expense I had sooner than planned with their early termination.  

Right now, you have $2,200 annually, so you're expecting the rental to be empty for a full month each year, so you'd just need to know your market to understand if that's accurate or not-Property management: it's normally advised to include PM in underwriting, in case you don't want to self manage in the future.

You may be able to do some arbitrage in this area.Unfortunately that's quite normal for military housing. 

@Kevin FitzpatrickReal Estate investing normally requires three traits to be successful - Money, Time, Expertise.Are you getting into the business with your brother in law because he has traits that you are missing?