Depending on what the gain will be, it may have been a good thing to do.Selling a property is a meaningful taxable event.

Another benefit of a Heloc is that you don't touch your current mortgage on your primary and  get to keep your current rate.

I'd be willing to live in it which appears to have some benefits for a condo conversion depending what town you're in.The thought being that we could buy a duplex/triplex/quad, convert it to a condo, and sell off the remaining units leaving me with (at the end of the day) an affordable housing option.Here are the condo zoning laws that I found for Sunnyvale: https://www.huduser.gov/portal...My understanding is that they don't do condo conversions with <3% rental vacancy rate, but it looks like it was 3.1% from the most recent HUD market analysis for my area that I could find: https://www.huduser.gov/portal...Does anyone know someone who has done a condo conversion in the Bay Area?  

But, if he has equity in the property , I would sell and get the $250k tax free gain.

Another important piece: you will not be in long term cap gains. 

If you just sell it, the first $500k is taxed at 15% as Long Term Capital Gains, anything over is 20%, No SS .... 

Regardless of which entity owns the shares (You or the LLC) you will have to pay capital gains when you sell the shares (If there were gains on the shares). 

In summary, do you think it's a good idea for me to partner with someone for my first deal, put in some or all of the money, take a smaller return, but gain knowledge and confidence to start on my own in the future?

capital gains tax, seller commissions , other fees, etc?

@Jeff Norton do a comparison of what benefits they offer vs costs against just opening your own.