I hate re-trading. 

You could like in it for 2 years at least and trade up tax free.

@Tanner MarseyI also live in SD and have been investing in this market for 25 yrs.It matters how much you own and when you bought.I bought a bunch of condos in 2009 at a 50-60 discount in the last 10 yrs they Jane all gone up 2x+In the last 15 months I traded 2 for 26 units in KS MO.

This way  I can manage the property myself (with some help from PM, because I graduated from Business Administration) so that I can learn the trade inside out.

That's highly doubtful.There are trade offs for liquidity.If a fund is more liquid than others, it goes to follow they'll have more capital in instruments that are easy for the fund to liquidate (e.g. money market, CDs, short-term treasuries/munis).The ROI of all of those asset classes is negligible and (currently) below inflation. 

Also, one benefit of cost segregation is trading taxes now for taxes later but of thought of a different way it’s better than that.

The knowledge you gain will be worth a lot more than the couple hundred you pay for the inspection and will probably save your butt at some point.I have a background in the trades, property management, restoration work, new construction, completed many transactions, self managed 20 units when I was getting started, longtime rental property and home owner etc. so I probably know more than most about buildings but I still rely on inspections in order to see the true condition of a property because you can only see so much just walking through, plus sellers lie and try to hide things.

Please explain in great details if you some of you have made that cross over, can it be done at any time or do you need the play the "rich dad poor dad" monopoly 4 green houses then trade up for the red hotel?

Pay attention to conversations where you uncover someone is a contractor or works in a specialized trade.

Even if nothing is for sale right now, I often find "dark trades" on RCA.