Keep in mind that sometimes there are properties with rents much lower than market that could drastically affect the property value if they were increased. 

Next, housing affordability will always be an issue for those with lower wages. 

Basically, how do I avoid the stress of watching a half a million dollar purchase disappear and the frantic begging for money last minute. 

Most rent-ready or good area 2/4 units are not cash flowing at the prices they are at right now but if you find one in a lower income area and are comfortable living there - then you could have some upside there. 

You can pay points to get lower interest rates with > 20% down no insurance.

With a good agent on your side, you're well on your way.I stress the importance of teeing yourself up for success prior to swinging, because if done right, house hacking can be one of the best ways to launch yourself towards financial freedom. 

I would try to lower my resell price since he is probably motivated as a seller and has earned two or three times his original price.The age of the house and all of the weather it has been through does concern me as well as the basement condition.( I might be a little biased because I've been in Dallas,Texas all of my life (for 61 years). 

Having to "come out of pocket" at all makes it typical to justify it as a  good investment.It looks like the only way to make this work would mean you would have to lower the price down substantially. 

When I sold it, paying off that loan, dropping my total debt, lowering my debt to income ratio, moving from 2 mortgages to 1, only increased my credit score by 1 point.I will NEVER under how credit scores work, but I know they affect chances of getting a mortgage and interest rates you can get.

Because most of the closing costs are fixed, the percentage can be extremely high on lower priced properties.