Ive seen this work well, as its not exactly clearly defined how long the IRS wants the holding period.

Remember, hard money loans are typically short-term (3-18 months), so make sure your flip timeline aligns with the loan terms.

I am looking into longterm vs short term rental options as well as financing options.

Not only that, the borrower got a pre-approved term sheet for $750,000 from a lender to refinance the property!!!

You are going to loose out on a lot of income by doing this .If your cleaner cannot complete a same day turn - time for a new cleaner You would if you were running a 53 acre ranch in Texas with significant additional logistical requirements and maintenance needs (both expected and unexpected) beyond what an average short term rental requires.  

Each market will take a different type of "energy" to be successful. 

and are guests mostly short term or mid term? 

I know one investor that recently sold off one of his long term rental investment properties that still had a USDA Direct loan on it. 

And if you need to rent in short term, that's fine too.  

This is easier to achieve for short term rentals, and a bit tougher for long term rentals - but I've been getting close for LTRs as of late (closer to 7-8% for LTRs).