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.

It heavily effected his under writing results.  

As I've mentioned in the past, I write for the "lurkers".

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. 

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

: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.

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.

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.