There may be a way to reach this destination in the nearer future that doesn't require 10+ paid off properties. 

Panama is about the canal and the banking industry, it's not known as a tourist/beach destination and it's a well-known fact that they've never cared promoting them as such.

Destin to 30A!

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.

The Destin market was down 30 percent last year in short term rental income from the previous year.

Hi Tricia,You are correct Lakeside Township and the surrounding areas are a very popular vacation destination for Chicago natives. 51 acres with R-2 Zoning would be a great development opportunity.

I lean towards low leverage by nature but it really comes down to what your plan/destination is in the long run. 

I also caution in taking on more than double the rehab expense you've incurred in the past - especially with a property that isn't tenant friendly from a parking standpoint; it won't be long before the trekking tenant discovers that trolling for street parking isn't the cruise he signed up for and starts parking in the yard, squeezing in the driveway, or starts claiming defects with the property so he can terminate the lease. 

With more professionals embracing a flexible lifestyle, our town has become an attractive destination for those looking to escape the hustle and bustle of urban life without sacrificing career opportunities.

9) Just some human-side stuff -- when you cruise properties, be kind.