They get a higher return since they are covering housing cost, have the $250k per spouse primary residence deduction in gains, is a savings account, higher leverage position, lower interest rate possible, will pay more premium for location, etc.House might be overpriced for REITs but not for home owners.  

Insurance doesn't cover anything anymore and we can almost just pay for all damages with the money we spend on it! 

Some properties appreciated double during this cycle and the rents still covered the mortgage after a cashout refi. 

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

So now we cover utilities for both units and the new tenant pays a higher amount too on the back unit to cover all the utilities with a great profit.  

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

However, in the off chance that I am not able to cover my gap funds (est. $200-$300K) from that small circle, how would you recommend I start branching out?

.#1 Please share the best general coaching program that covers all the Real Estate Investment domains.#2 What about the best focused coaching program that covers Wholesaling.Also, is there a list where these REI coaching programs are listed and rated? 

The down payment and I'll cover the rest with renting cash flow.  

If the insulation is in decent shape and not covered by combustible insulation, and not terribly overloaded, it might last many more years.