I have the same idea for my son as well.

We keep a daily updated list of all active and eligible STR's for sale and currently there are well over coastal Oregon listings for sale with vacation rental or STR AirBnB eligibility and generally focus on properties that can reliably secure a permit within 30-60 days of closing.

Additionally, try collaborating with local businesses like spas, wellness practitioners, yoga, wineries/taprooms, etc... and try some messaging with them around wanting to promote them in your blog and on your property.

Since this is an unconventional lending instrument, you have to make sure all your ducks are in a row (contractors willing to perform the work, dates of work start/completion, all additional paperwork completed, etc), but it was well worth it.

I have properties with swimming pool and playground so I am well aware of the risk management side but a winter item like this is a new for me! 

I have a few commercial realtors that I reached out to, but thought that this community would be great to reach out to as well. 

Is this something you have experienced as well, how did you deal with it?

Most new development is well over this mark and, since there aren't likely to be many more complexes built that offer decent living conditions for lower-end rents, there is probably some room to raise Class B/C leases in the coming years as more people move into Louisville.And, if things do decline, the "luxury" crowd is going to be looking for cheaper digs. 

Well I adamantly disagree. 

Like someone else said earlier the terms of financing can vary significantly based on the lender, as well as the strength of the borrower or the specifics of the deal.