3) Poor marketing / sales.  

@Janki Patel, Your old partnership needs to take title to at least as much real estate as it's net sale in order to defer all tax. 

Have the loaned serviced. 

Do we have to create an LLC after the JV is signed?

My wife and I are in the same boat right now, dabbling at listings or off market whole sale "deals", or paying down RE debt.

You are right, wholesaling is marketing and sales.

In small college town with high rental demandAsk price 745kGross rent: 9750/mth 177k/yr     (differed maint properties with potential 200/mth per unit increase once renovated) estimated reno (190k across portfolio)NOI: 91,475/yr   (12.6 CAP)    (includes tax, ins, listed maint for past yr)     After reno NOI 127,475/yr   (14.6 CAP) Deal info:    - Owner finance 745k 20yr at 6% 20k down minus deposits (~13k)Cashflow  = 2100mth     (self-managed) (self maint similar to the previous owner)By this alone, 2100 cash flow added per month, it will put me at my financial freedom number of monthly cashflow is equal or greater than my families spending amount.

What are some of the considerations or pitfalls to this strategy where we would start renting a single family residence out, then convert to our primary residence after ~5 years.

However after switching around to a couple when my team got started as we scaled to 80+ guesty was the clear winner.  

Heloc / Cashout Refi after a few years and purchase more properties in the Milwaukee / Ohio areas.