The issue we are running into is that lenders are not recognizing the excess amount he earns as income, therefore it looks like he will not be able to afford any loans that he would be approved for.

Hope you don't put down large earnest money deposits... these guys will make sure you lose them! 

Some properties actually lose money each month but gain value through appreciation.

The least states:"Tenant shall pay a "late charge" not in excess of five (5%) percent of the amount in arrears for each month the arrears remain unpaid if any Rent is paid more than ten (10) days after the due date thereof, to cover the extra expense involved in handling delinquent payments.

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

It may be that they are underwriting the property at a significantly different valuation than what you are using or that they feel that you or the deal is excessively risky.

If you put the house in her name and you have siblings or other folks who would have a claim as a direct heir on her estate, you run the risk of losing the property to another heir. 

With the equity you’d free up, paying off $50k in personal debt and boosting your credit score while freeing up $3k/month sounds like it could significantly lower your stress and open doors for future projects.That said, selling means you’d lose a cash-flowing asset, even if it’s not huge.

Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

Quote from @Brandon Croucier: The loans are available but nobody wants to do them.There always seems to be something wrong with the properties, as lenders we just can't make enough $ for our time.9/10 Borrowers also complain about the "excessive fees" for the loan amount.If you are okay with paying 8k in closing costs then the loan is available.