However, if you can flip it and make a solid profit higher than what you would get out of a cash out refi and/or rents won't cash flow, then flipping makes good sense (unless you need a tax write off but since this is your first investment, that probably isn't the case).  

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.

In many cases the mortgage company writes off the loss or goes after borrower depending on if they have other assets - if they do then they are gonna be coming after the owner

It heavily effected his under writing results.  

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

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

Its also classic and never goes out of style.

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

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 have helped finance some of these style loans.