There's < 2 months of seasoning for the purchase, cash into the deal is ~$975k w/o rehab (minimal planned so far - turnkey), purchased the property for 35-40% below assessed value, 825+ FICO, and would optimally like to pull out $975K-$1.15M of equity.Main scenarios we've thought of to accomplish this are: 1) structure sale of property from SMLLC to self and secure 30-year new purchase financing on deal (unsure if legal and tax implications if above initial cost basis)2) delayed financing (LTV restrictions a concern)3) cash out refi (seasoning concerns)4) DSCR (seasoning and rate competitiveness concerns)5) one of the above plus a HELOC, personal loan, etc.?

I like the product but their policies drowning them down in competition.

You want to be competitive but also make sure you’re covering your costs and hitting your financial goals.How Can I Make Sure That I Do Not Rent the Home Out Under Market Value?

Definitely compare hotels as part of your competitive data set (comp set) as lots of tourists will consider both. 

York/OGT is very competitive.  

  $250 is about the average of what our competition charges so this is working well for us right now.

Go to MLS.1) As if there is no competition on MLS?!

Before you make your decision, check  Furnished Finder to see what the competition looks like and how many have wide open calendars to get a sense of supply & demand.

I like the product but their policies drowning them down in competition.

Any market can work, you should consider a market that you have some 'competitive advantage' compared to others.Think of an area that you grew up in, went to school, visit friends / family, visit often, best of luck.Also, do you have any experience in rentals / short-term rentals.Air-bnb's hosts have become 'commercialized'.You will not out-perform a host who has years of experience, does this 24/7 and has a team of support.Best of luck.