Rental property newbie with questions

[Bret Benton]

Being my first post I'm just looking for general information.  I am young (28) looking to get into long term rentals as investments for the long run.  I am in a location where I feel this would be a solid investment.  (through lots of research and conversations with others experienced in rentals)  My first house I bought back in August of 2014 will be my first rental property.  My intentions are purchasing approximately 5 properties over the next 5 years for my long term investing.  I have a few questions....

1. I founded an LLC around the same time I bought my house. This was to be used for small construction projects on the side (full time employment is in construction) but it just didn't turn into what I expected it to. It seems like running my properties through the LLC will be the way to go for liability purposes. How is the best way to do this? Use LLC as property management firm? Transfer property I have purchased as individual to LLC somehow? If so...how? Any help would be greatly appreciated.

2. I am in a lucky situation where I should be able to save approximately $20k over the next year for a downpayment on my 2nd property. Should I look at outright purchasing this through LLC? How do I go about finding financing for 2nd property with liability of debt still there on 1st even if I show steady rental income? Once again general info would greatly be appreciated and things to look out for/questions to ask.

3.  At what point would you consider letting property management company handle properties?  3, 4, 5??  etc. etc.  

4.  Any advice to look out for being a newbie as I am expecting to run into many bumps along the way.  

Thanks for any advice