@Alex RodgersIn a competitive market, it might be difficult to find cash-flowing properties, but there are a number of tactics and methods you can take into account.

Was I too close to the mentor and presented competition?

The only benefit I see is that it provides at least some competitive counterbalance to ABNB. 

But they ARE your competition if trying to wholesale, unless it's a big flip.

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.