You can also look for what is called a form based code and a good indicator of development, few cities have these, but they tend to bring about big change.I hope this helps, I tend to delve into this stuff on a daily basis because I work in Urban Planning and Urban Design.

Debt/Income Ratio - this could be a problem as you indicated... good thing about FHA is that you can use family money as a "gift" for a downpayment so I would recommend the same thing Cory did above with borrowing from your parents and paying them back using cash flow.3.

What does that indicate?

There were a lot of people indicating to steer clear of them so I was apprehensive.

Trends are great but sales price alone is not the sole indicator.

1/7/2016  Wesley - thanks for the post and  creating some good thinking ..... if you are desiring to  purchase a  primary home ....its  likely to not  get any less expensive in the  future ....so if you are waiting for  prices to come down - this might be a long wait .....if  you buy a condo  and  want to use a FHA loan  to minimize the  down payment - be aware that  the condo complex will need to be FHA approved  ( not many are any longer ) ...that being said there are  some conventional loan programs  that allow as little as 3% down . 

I would like to know what are some indicators of the difference between needing a little work (<5k) or a lot of work (>20k). 

Major kudos for getting out when you did and minimizing the damage.

I say spend the $500 and have a reputable licensed environmental company do the soil test around the tank to give you some indication of any potential leak.  

It is not so much indicative of me jumping the gun, but rather an effort to establish working relationships with the necessary individuals and "building a great team" for my investment path.