Would it be better to try and put a business plan together and pitch to private investors or a bank? 

@Michael Stanley NinoHaving 40k for a downpayment is a great start but remember for a conventional loan banks will look at Credit Score , reserves as well..

@Sherrod Mcgowan-green My paycheck is automatically deposited and split between 2 bank accounts.

Can the bank go after him for the existing mortgage or will he just never be able to take a loan out against the property with the existing lien? 

Like when you go to a bank and they charge you a mortgage doc fee.  

Note: the Amortization can be shorten if the property agent is older, some banks will go out to 25-30y Amort if the property is 1980s or younger.and will only go 15-20Y Amort if older then 1970s

Start by looking for hard money lenders and talk to smaller banks and credit unions.

@Karam A Tascoe yes its based on comps but I am more referencing your bank-ability.

It isn't that i'm not curious what the appraisal would come in at, but I will likely be getting one when i go to refinance in 6-18 months and all the value would do right now is: 1) Give me a more accurate idea of what the bank would value the property at2) Delay closing as appraisals are 3 weeks out minimum right now3) If it comes in high the seller could use that info to back out4) Add additional costs (around $950) to the closingP.s. - I will still be ordering an inspection.Thanks in advance!

My goal is to acquire as many houses as possible and become a mini bank.