You can do both (though I wouldn't attempt to file business taxes myself), or you can do the bookkeeping and hire out tax prep, or you can hire out both.

Another strategy is looking at short term or mid term rentals thats one way to cashflow but it does take more work as your basically running a hotel business but once you figure how to automate things it will get easier at least thats what the short term rental investors tell me lol.

Every condo will have assessments at sometime.HO6 condo insurance isn't the product to be used for a STR.

Are you a realtor looking to increase business?

They have to in an effort to make the business profitable. 

I feel that if both parties understand the risks; if real estate investing is their business, if both parties are sophisticated and experienced investors, and both decide the risks are worth taking, then subject to can be a workable tactic.  

But an amazing business model. 

I recommend you attend a demo webinar before you decide on a product.

Appreciate your feedback.Another question I have is related to Cashback from the business credit card.

I did not know that most DSCR lenders don't prefer a business model aimed towards student renters.