Its never too late to make money, things can progress as fast as you want them to. 

However, if the maintenance issue is an bigger one, I usually need to make several trips: Check it out myself first, meet someone to get an estimate, check progress of work if it is over multiple days, review final work, etc. prior to paying for the services.

Agree with @Brett Russell in his assessment. 

Then people from the insurance company will have to assess the inside.  

Just by this very basic assessment, picking from the two, focusing on flipping contracts on houses + long-term buy and holds on commercial, makes the most sense.

Does the building need maintenance which will require the HOA to hit you with a special assessment?  

my dad says Everything has to dried before insurance has to make its assessment.  

my dad says Everything has to dried before insurance has to make its assessment.  

There is some serious investment knowledge being shared here.I'm from Houston and currently invest in single family homes in my area, but as I progress in experience and cash, I would like to go full steam into commercial retail strip centers. 

Using "the right" info is best.To find out what the "right info" is, I would suggest taking some real estate courses at your local university, a couple of real estate appraiser courses, and or get your brokers license.I have brokers licenses in CA and TX and CCIM in progress, which have helped gain credibility/knowledge/expertise.