These places will be more expensive, for a reason.Now I do think that there is some opportunity in certain areas of upstate NY for short term rentals, however upstate NY is not a well established travel destination so your occupancy will probably be low and highly seasonal but this method is viable.

Also there is no seasoning for time needed to move into an LLC, there are just seasoning requirements on cash out refinances, but most lenders have no restrictions on these after 6 months.  

They have great colors of the year, of the season, and accents all the time that can help you make it a little more refreshing.

Carolina Beach since you're already invested in Wilmington and know what to expect from that market.AirDNA is showing Carolina Beach to have greater overall rental demand and investability, though it is extremely seasonal.

You just have to season the funds which means get it into a savings account 3 months prior to the purchase application.

Since you are a seasoned stock investor, then I'm sure you will agree with the following phrase: "Timing the market does not work, but, Time In the market makes all the difference in the world!

If you are looking to refinance with a rate and term or non-qm option you may be looking at around 6 month season.

I'd like to list ASAP so as not to miss peak summer season. 

The high season is May/June/July/Oct.  

I'd find a lender that can do deals with brand new companies and do not require seasoning, if you choose to go that route.