Also, I'm gearing up to move forward with my first flip I have a private investor I've done tons of research (Big BP fan) Ive analyzed deals (only on BP) after deals, i just don't know exactly were to start?

Here are some alternatives to commingling your assets: using the Solo participant loan feature to do the deal outside of retirement funds using non-recourse financing from a lender or private source in combination with retirement funds as the down paymentusing your 401k or IRA and partnering with non-disqualified persons 

Until something goes wrong.I have sold clients A and B apartments in PDX  these are 5 to 10 million dollar size apartments.

Just for giggles, maybe he started by wholesaling and made enough to buy his first place that way.So he wholesaled maybe 10 properties netted himself maybe 50 K, used that 50 to buy his first multiple , then he added some value held it for a year , then sold it for a gain on his money of lets say 85 K, and during this time wholesaled 10 more properties giving himself 135 k.

Such as a 1200 SF house that sold for $25,000.

I regret every single rental property I have ever sold!

I just recently thought of this since literally in my neighborhood my exact home floor plan and layout just sold over 279,000 and another comparable sold 270,000. 

No pictures of the inside are available and no walkthroughs or inspections are permitted as it is occupied and being sold "as is".

I have bought, held and sold over 20 SFH and duplex units in my previous real estate "life" as it were.I realize that analysis paralysis can be very real, even more so for someone like myself that needs to see numbers that I find attractive and reasonable. 

So lets say you bought for 500k and sold for 800k [300k capital gain] could you then deduct 200k (2/3 of the 300 k capital gains since you lived in the 2 out of 3 units???