Maybe the "classification" isn't the important piece - but can I write off expenses if I occupy a property more than 14 days?

Training will be however the broker has it setup.Even around me, as I recall three Re/Max franchises/brokerages neighboring each other have widely varying bottom line fees, different split structures, different tools (e.g CMA tools or Dotloop vs DocuSign). 

Some of the ideas I have came across after the searching these forms and talking with friends that have had success in RE are;-Out of state investing (may be best for cashflow?)

Would like to be added to buyers list or make connections for existing or future deals.

Depending how much you earn you and how much extra time you have available you can step up those savings by getting a side-hustle in any part of real estate....working for a top Real Estate office on weeknights and weekends, working for an RE Investor, working for a General Contractor and learning a few skills, etc.

There's a part of me that hopes that in writing this, it will somehow make it much more real - so here goes:My five year plan in action (2014-2018) - what's yours?

Via the accountability group, new connections were made and we plan to stay in touch and potentially partner on deals in the future.

My thought process is that this would be an equity play but am worried that I would be handcuffing myself for future investments.Option 2 House Hack with Partner: My friend/ potential partner is looking to do the same thing.

If so you would want to come to an understanding on who maintains the "improvements" and get that in writing. would love to see some developers jump in on what their experience is. 

Most states do not factor in losses from other states when calculating their taxable income.However, yon't think you lost out on the state where you have a loss. that state will normally treat that as a loss that you can use in the future when you sell the property or have rental income.