The ultra expensive luxury homes won't be hurt as much.3.

Vacancies are minimal here but the secret is to have good photos, a good story, ultra-clean space, and pricing that entices that first guest that changes with seasonal demand.The best thing about short term rentals:  they can be long term rentals too - if needed.Hope this helps.  

I think there are plenty of places to achieve that happy medium, especially if you are the sort of person who doesn't have to live in an ultra-hip part of the country for either professional or preferential reasons.30 was my "retirement" goal, but I've amended it to "as soon as practical" :) For me, that is $30k+ yearly "passive" cashflow, since I can personally live on that and remove the necessity for a conventional job. 

Remember they make money on you guys that pay them and never do anything which is 90% or more of the people that engage him. these wholesaling type programs are so location specific... you can go to Detroit and wholesale houses in your first 3 hours there... were you and I live.. its very very tough.. there simply is not the  inventory.you may notice the wholesale crowd that boast of success is almost always in areas of the country that are old mid west rust belt cities were there are literally thousands of targets for you to work... 

Biggest piece of advice I can give is to be ultra-conservative with the ARV and buy right!

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Retirees that want ultra security and are wanting to live off of the income and keep pace with inflation.3.

The one agent I know in SoCal who does high end properties has mentioned that the commission there is typically 5% (2.5% for each agent), so this is pretty much in line with that.I imagine for the ultra-high end (like this property), commissions could be even less, but remember that at this price range, the agents are taking a risk as well, as they often sink thousands into marketing the listing and if it doesn't sell, they lose money.

Avoiding ultra-liberal markets.

I am interested to see if you can do deals in a ultra-high price market like LA.