There are little pockets that can be very fruitful to an investor.

You always run the risk of running afoul of a "prohibited transaction", you have to maintain % contribution into perpetuity.....Again not to say you can't partner with your IRA, and I would probably do it again...just make sure the juice is worth the squeeze on it because it's a whole nother bag of worms to deal with.

Everyone wants the low hanging fruit.

I don't see huge upsides as there is only a few years left in the up swing and after transaction costs, it's not that fruitful to buy now and hold for another 5 years or so.Also, I'm in earthquake country and insurance is a gamble at best as they may deny a claim.

Flipping is a self-employed job with high risk and high transaction costs.By the time taxes and agents are done with you, the juice is rarely worth the squeeze.   

The smaller platforms will probably account for only a fraction of overall bookings, so the juice may not be worth the squeeze. 

I suspect Oakland does not have the juice to enforce this.

Paying SEO can be expensive and not necessarily fruitful.

That is a cardinal sin.You should look at marketing the same way you look at the contents of a fruit salad.In a fruit salad if the only ingredient in the bowl were apple slices one would have a hard time calling it a fruit salad and only those who liked apples would enjoy the presentation.

Here's a fundamental explanation to get your juices flowing:Assume a house costs $200,000 and rents for $1,500.