I'm not a CPA so you should consult with yours, but these are the basics for your situation.Capital gains exemption on personal residence - This is the 2 years out of 5 rule, if you've lived in a home as your primary residence for 2 out of the last 5 years you get a capital gains exemption of $500k since you're married (it'd be $250k if you were single) Meaning the home can appreciate $500k or less and you'll pay no capital gains as long as you meet this 2 out of 5 requirement.

If they were really too good to be true, you wouldn't have to pay attention to them. 

Pay attention. 

His accountant has told him that it would have to be a land contract to defer capital gains taxes.

My tax bracket with SS and rental income from LLC or IRA will put me in 24% tax bracket.1) Can I move IRA rental properties  directly into a Roth IRA, or do i first have to convert the IRA rentals into cash pay the capital gains move cash to the Roth?

v=AFIxi7BiScIA video from DW TV about Wealth people and middle class - pay attention to the super wealth real estate investor, immediately I turn a fan of that "monster" .. watch the video.my name is Thiago Zanetti (TZ is fine since no american I met yet can say Thiago correctly :D )I have been listening to the podcasts daily, reading some books, doing some researches online.In 2000 something my father gave me Rich Dad Poor Dad, that consolidated my idea of starting a business.I own Fly Shop Brasil - Brazil's premier fly fishing shop.Ok, that's my introduction. 

. $100k gain right now is tax free, If you simply sell.....you’ll lose that if you redevelop it.Builders know how to do this, and their cost for doing it themselves will be much lower than yours.  

Just listened to the BP podcast with Charles Roberts, where he mentioned how important it is that you gain an understanding on the subject of financing, as it is just as, if not more, important than understanding how to find deals.

Personally, since Bay Area RE prices are high right now, I'd sell it and take advantage of your homeowner cap gains exclusion--- and then reinvest capital elsewhere. 

We currently own a new house that was built before we moved in, and it is in a developing neighborhood, we are going to rent that house out then move into the house we just bought and do a live-in-flip and possibly sell or rent after two years to avoid the capital gains tax on the profits.Our goal is to get as much stuff done to the house as we can before we actually move in because we have two small children and it will be rough trying to live in construction zone with these two crazy babies.So, so far we have taken out the whole kitchen, removed ugly tile in the living room and two bathrooms, and started demoing the laundry closet.