I dont want to be saving money my entire life because that savings account wouldnt be working for me I want my money to work for me!

Definitely use separate accounts, whether you have an LLC or not.Checking: receive rent, pay billsSavings: hold deposit and reserves for capex, maintenance, taxes, insurance, etc.When your checking account has more money than is necessary to pay bills, transfer the excess to the Savings account where you can build funds for a new investment.

A yr later after saving and going back to work I decide Its time to buy another..

I'd like to save him that pain).

All I know about his finances is that he has some savings in a savings account and is almost entirely risk-averse; despite that, at the end of discussing it with my father, my brother blurts out that he was willing to invest in my venture as well!

@Devin Borders - I can't speak to if there is a legal way to both assume/pay their mortgage and fully protect yourself, but I am sure there are others that can.One thought I had was if this property is off-market and ~$220K in value, I'd offer much less for the following reasons:  If you can do this without realtors (if it is not currently listed with one), that would save the sellers 6% in commissions (~$13k).  

A nice carpet (not the standard rental brown crap) would save you $ and might still attract the buyer you're looking for. 

Not sure how depreciation will work or how to get the best tax savings.

(my opinion).I think that you may have left out some expenses, however, you can save money if you self manage.My first comment is that you can save money if you manage this property yourself. 

Go ahead, efficiency is the way of the future and they will save you good money.