Stalk them on social media, call employers, previous landlords (not current), follow up every lead, and zealously chase trails of smoke to see if there is fire.(2)  Insurance:  This is water under the bridge, but I'll bet the increase in premium you would suffer switching to a more expensive carrier for 24 months would be MUCH LESS than what you paid for the roof. 

I suffer from severe analysis paralysis from what could go wrong and what is the "best" method for what I want to accomplish.

Columbus Ohio is likely to suffer from its higher than average exposure to retail in the current economic conditions.

Find niche of syndication/flipping/rentals  My current career pays me around 100K - I have thought about getting into real estate many many times to make myself more familiar with the arena/people - The idea goal would be to work with investors to help find and analyse large deals or someone who is currently in syndication - My current state is 30 years old and about to be married - with current bills obviously in the short term this will cause some suffering thought for the long term I know this option could offer a much larger pay off.

At the same time, vagrants suffering from drug and alcohol abuse are for the first time pitching tents on our street.We feel trapped between falling rents and falling home prices, rent control, and bad city policies on crime and homelessness.

Many people never develop a plan and suffer years later as a result.  

This is definitely the area that the agents who throw up a sign and take photos with their phone are going to suffer.

IE create company that does it for a living dig in and workAnd RARELY works if your targeting properties in an MSA at 50% of the median price point.. those are priced for risk and you will suffer the risk of owning them 95% fo the time.  

Education never suffers in a recession. 

Maxing out the HELOC to purchase (your first step) will make the FICO go down about 11-14 points for 60 days so the rate on the refinance second step may suffer.