Given this is your first investment endeavor, I would highly recommend going with an experienced and reputable management company that will mitigate your risk when the not-so-fun parts of property management arise.

My credit card companies will direct deposit the cash into my bank account in a day or two upon request.

They are property owners in your neighborhood, not an external company with no stake in the community other than management fees. 

In my case, I have residential rentals in one LLC, commercial properties in another, self storage in a third, and my real estate company operates in a fourth.

Any one that can help me with a policy?

We have 2 LLC's that run management companies and 10 LLC's that do real estate investing.

The company never paid the $ on time, but eventually always came through. 

Is it legal to do an off-market transaction straight through the title company without using the agent? 

There are companies/agents that specialize in what you are looking for.  

First, I'd try to find why the water is doing that as you can replace the siding, but if the water is going to keep doing it, you will have that problem again.If it is isn't a condo, I'd talk to your insurance company.