Which have been my original main focus, but those cities are getting expensive and when the price is within reason I’m finding a very high crime rate…will keep searching…

Also this emotional pressure is really common with high pressure sales environments, which is often the case with large wholesaling organizations. 

There is a high percentage chance that those closing costs are actually going to buy down their interest rate.

Is removing black mold from the basement a high priority in most cases? 

Make sure the condo fee is not too high.

One quick solution that jumps to mind, until a bigger opportunity presents itself, would be food/coffee/beverage truck or trucks. 

I'm looking to get a loan for my first non-owner occupied rental property but my current lender is telling me my debt to income ratio is too high due to my student loans and mortgage.

First someone new will be living with you and that requires adjustments.Second it's not just someone, but rather it's your in-laws which can bring stress to any marriage good and bad.Third your introducing a money factor into a highly personal relationships. 

3 bed, even smaller, that's newly updated is quite rare in the Boston market at an affordable price so if its easy enough to do I would highly recommend it.

@Min Zhang I have tended to look away from my local market because of the high market prices.