This strategy, if combo with REPS (real estate profession status) basically checkbox on your taxes is key to canceling out full-time W2 employment.If this is new to you... 

If so, would this still cause issue with the S-Corp tax rules?

The slightly confusing part is the Business License Tax Certificate.

Is there anything different in terms of STR tax loophole if I do STR by the rooms?

Your projected pro forma will use your updated costs (such as increases in property insurance and taxes, upcoming repairs) and income (increased rents or added income streams).

People should recognize things never get cheaper (which is why now everyone should roth 401k that savings because I would rather pay taxes on it now than in 30-40 years)... 

I may want to do a cost segregation study and look into tax benefits.

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.

My goal is to create a scalable entity structure that balances general risk and tax liabilities. 

When you guys are filing property tax amounts for rental properties, what figures do you use?