He's on SSDI (Social Security Disability Income) at just under $1,500 a month and he wants to do some wholesales to make some extra income.Lets say he does a deal or multiple deals and makes any assignment fee on it/them and the profit exceeds 1.5k which is higher than his disability per month.

Secondly I would look into if it make sense using realtor or not, there are markets that it makes sense and there are markets where unless you as the owner are paying agent fee most will pass. 

Expect to allocate less time  towards management functions if self-performed or more favorable management fee structures if 3rd party management companies are utilized (which ties back to #1, as well).

Usually a primary home is going to offer the best option to borrow against for higher LTV/CLTV, lower rate, and less fee's (No points).

Live in new home while it appreciates for 10 years until I get a faculty housing spot, sell private market house, put proceeds (minus downpayment) in bank for retirement (I estimate this will be 1.3 mil before capital gains and real estate fees based on 7% growth in a very desirable Southern California location), and take out new loan for lower cost faculty housing.

The fees vary with the specifics of the deal.

I personally like the credit card balance transfer check route, since it's interest-free for a decent amount of time (aside from an initial 3.00% fee). 

I found a buyer for my home, got a payoff statement from the mortgage company stating the payoff was $247,000 (principal at $233,000 + fees and charges), the buyer was willing to pay $271,000.

I thought better to terminate in the middle of repairs prior to them completing everything + Owe appraisal fees to Lender.  

It's free, handles rent payments/reminders/late fees, maintenance requests, some reporting (e.g., P&L), tracking expenses and income, rental listings, lease signing, etc.