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.

Are you a realtor looking to increase business?

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

It's great to see interest rates "level off" at something workable for hopefully all parties...the volatility over the last several years has been tricky to navigate...Chicago hasn't had as many market fluctuations which has been nice.

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.  

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

To avoid paying capital gains on the sale of the rentals, the most straightforward way is to complete valid 1031 exchanges on your two sales.  1031s themselves can be a little unintuitive to navigate. 

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

It’s basically applying for several business credit cards with 0% interest until we have the amount we need.

if the private sector operated this way, they'd be out of business really fast.I'd just rent it out; you did what you had to do.