Normally people do not like to move in the Winter, and the prices are usually lower that time of the year.

When building new, it is possible to design and build houses, and larger buildings, with a modest increase in up-front capital (10 - 15%) costs in comparison to the "normal/typical" minimum code build, which have resulting energy consumption 70%+ lower.  

You make sure what is being represented by the listing agent is factual.. and or you have your license on the line for reps and warranties..I know you work with a lot of out of area clients... but you live and work in the community like a normal RE broker would do... are there any brokers in Cleveland selling homes in Venice beach ?

Normally, this is estimated around 5% (but may vary based on age of the property, up front renovations, etc.). 

Remember that everything you'd normally do as an operator has to be thought of at this stage.

The process is very similar to a normal loan and I decided on $50,000 on 2 properties ($100,000 total).

Sounds to me like normal wear and tear from them living in the house (probably kicking the screen or something stupid), should be up to the tenant to keep the property (the screen) in good condition.

Its normal to be terrified when making such a big decision!

Always remember to do a math analysis on your selected possible property and try to look at it before you make an offer on the selected property or at least have a clause in the sales contract that will allow you some time (about 15 days) to inspect the property and possibly get out of the deal without much of a penalty that won't hurt you.Just select what is normal for that neighberhood and do not over-rehabilitate.  

I believe your point was more about if you are a W2 and expect retirement savings if you are lucky with your 401k to get you to where you want to be when you retire then yea, that is taking a gamble given the access to wealth building vehicles that are possible in today's world.