(Britt Theater)Ashland - WINNER to me, but like Jacksonville I think I would do short term rentals there, take advantage of Shakespeare festival (Fall/Winter), Britt Theater (Spring/Summer - Jacksonville), and Mountain Skiing in the Winter.

Iḿ in Snowshoe WV  ski resort and its went well so far.

Usually for us... direct mail is a last resort because the conversion rateWe like to txt and call with sellers/buyers and if its a deal of a lifetime(assuming seller doesn't answer phone), then we would do direct mail.

A primary residence is where your mail is delivered, where you have utility bills in your name mailed to that address, where your driver's license says you live, where your w-2 and IRS etc. are filed.A second home is a part time owner occupant and is usually 100 miles away and in a resort area.Four units in another state while you own single family where wife lives is not owner occupied. 

Selling is usually a last resort solution in my opinion.

We currently have $40,000 saved, we can cash advance up to $3,500 on our credit card as a last resort.

You can treat this like a business and be respectable and not a jerk-off about it without resorting to payola. 

Purchase price: $42,500 Cash invested: $40,000 Sale price: $270,000 Double wide in RV resort with rental spot that had great view of water and high square footage of parking.

FYI In Colorado the ski resort communities are blaming STR;s for affordable housing issues.

The local ski resort here recently posted that they were canceling the summer concert series because they couldn't find workers "even though we're offering great wages and a sign-on bonus".