The heavy cleaning and repair costs after longer stays are definitely pain points but I've seen my clients make it work by screening the tenants more carefully for MTRs, doing bi-monthly checks to catch issues early, and writing clear lease terms about maintaining the property.

Am I required to hire an attorney to write up the contract and assist with the closing?

It heavily effected his under writing results.  

Not every lender can write mortgages in a way that support our transactions. 

He jumped on the short-term rental bandwagon, hired a property management company to handle the day-to-day, and hoped to write off a hefty sum against his W2 income.However, his journey took a turn for the worse when he got audited by the IRS.

:This is where the contract between (or at least having something in writing) would come in your favor.

Assume that you could meet with the CEO and give him some direction or write articles about how great the stock was and cause its value to go up. 

If you place your rental (STR, LTR, or  MTR) into service by the end of the year you can begin to depreciate the property and write off certain expenses.

I've been working with job titles like construction project manager, who doesn't know a lot about construction but coordinates architects, engineers, GCs etc, the VP of RE management, who also does not know a lot about construction but oversees site selection, lease negotiations, property management, RE accounting who writes my checks and does annual CAM audits, and other jobs like that.

As an investor-focused agent in the Cleveland market I always have my clients write the following contingencies in when buying a house that's tenant occupied:1) Offer contingent on home inspection- usually a 7-10 day contingency period, this contingency allows you to either A) move forward with the deal B) renegotiate the price if issues are found, or C) walk away from the deal2) Offer contingent on appraisal if you're going financing3) Seller to provide copy of current lease agreement4) Seller to provide a rent roll/tenant ledger with proof of payments received5) Seller to provide copies of 3 previous months of any utilities paid by the landlord6) Seller and tenants to fill out Estoppel Certificate.