Everything you saying is echoing what I believe.Accountant by day 9-5 and own about 13 units between a few buildings with my lady and recently got into fix/flip in order to scale.Sounds dead on.

It is very much case-by-case and requires understanding of the current regime for personal itemized deductions, as well as gambling on the proposed changes to this regime by the current administration.

The reason I stayed at the Banana Bank Lodge this time, is because the Lady is a world class artist, thus an artistic eye. 

The plan is to put the rentals in SCH E of our joint return and file with TurboTax-We live in Florida-Leases under my wife's name, Airbnb app under my name, dedicated bank account for all rentals activity in the name of both-We have umbrella policy for liability protection for the rentals-We leverage some contractors (for example cleaning lady for the Airbnbs or lawn maintenance guy) that we pay >$600 for their services in a year and they are not our employees.

For example, I know a lady in my local market that is very successful in the land business and has developed a niche that cashflows very nicely, without a lot of stress, as she puts it though I can't imagine how that is possible. 

Quote from @V.G Jason: Quote from @Jay Hinrichs: The mindset of cash flow is everything and appreciation is just luck or gambling or whatever these folks say is one of the worst mindsets I see on BP.

Simple appreciation is a gamble because you have no control over it, so don't consider it.

And you use a cleaning lady who spends 5 hours to reset the property for the next guest.

It seems like there should be a dividing line somewhere to make it easy, but also maybe not because both of these ladies seem to have pretty solid claims although I would think the last one has a better shot.From a legal POV (although this is not legal advice although I am an attorney), without a will the estate gets probated along blood lines.

In a waterfall, the GP is incentivized to stay the course, gambling the LPs equity, because the GP only makes money above 7%.