Some stories are too complicated to explain just on a forum but happy to share if you would like in a DM. 

Having sold over $200 Million worth of this stuff I can say without the slightest doubt that, that's the more accurate predictor of performance than what some Joe DIY did or didn't do.It's not really as complicated as you guys may think.You've got your gross income folks.

Investors are advised to consider more traditional real estate investments and to educate themselves thoroughly before diving into the STR market.It is actually way way more complicated to have STR in Lake Tahoe rather than in Hawaii ….

And there is no function at all to import transactions from my property management companies, so I need to keep a separate set of books for things I pay and then have my accountant manually reconcile my books with the property management statements at tax time.Fourth, it's incredibly complicated and hard to learn, but the customer support is very limited and rarely helpful.

This gets complicated with two sets of participation rules for limited partners and individual taxpayers.

To deal with any problems and safeguard your investment, create backup plans and risk-reduction techniques.

@Spencer Speckles,  there are additional complications if you try to carry back a note while performing a 1031 exchange. 

I'm not sure most brokers would allow people to do both, but not sure about that.Personally I have more than enough to do on the real estate side, I don't need to complicate it any more by adding mortgage. 

Try to use a few different techniques to see which one is a better fit for you. 

.- rentals do not go under an S-corp, which is why a separate PM company was suggested- S-corp technique on reducing SE tax is both tricky and costly, and you cannot set up your salary arbitrarily- you can only base your 401k on the part that IS subject to SE tax- you usually cannot generate enough "earned income" from this 2-companies setup to make it worthwhile for 401kSee, it is not simple.