According to the data Winter Garden is "Size/ranked" 150.

First, look at lists of cities ranked by employment, employment growth, net in-migration, cost of living and other economic factors and find the top 3 on those lists and then start looking at properties and neighborhoods in those cities until you find one that grabs you.

Many OOS investors set themselves up for failure because they don't truly take the time to understand:1) The Class of the NEIGHBORHOOD they are buying in - which is relative to the overall area.2) The Class of the PROPERTY they are buying - which is relative to the overall area.3) The Class of the TENANT POOL the Neighborhood & Property will attract - which is relative to the overall area.4) The Class of the CONTRACTORS that will work on their Property, given the Neighborhood location - which is relative to the overall area.5) The Class of the PROPERTY MANAGEMENT COMPANIES (PMC) that will manage their Property, given the Neighborhood location and the Tenants it will attract - which is relative to the overall area.6) That a Class X NEIGHBORHOOD will have mostly Class X PROPERTIES, which will only attract Class X TENANTS, CONTRACTORS AND PMCs and deliver Class X RESULTS.7) That OOS property Class rankings are often different than the Class ranking of the local market they live.8) Class A is relatively easy to manage, can even be DIY remote managed from another state.

What if you do not rank #1.

You could also just use SEO.For a small town like that it should be too easy to rank #1 and dominate.If you do that, not only don;t you have to go to your town and do all the work to get leads and then send mailers to them, you also wouldn't have to pay a cent for these leads.SEO is weirdly pretty much unheard of while it is the absolute best way to get leads/deals hands down without exception.No effort!

Mountain communities are experiencing the same appreciation we're seeing all along the front range. 4 of the top 5 places to live ranked by US News for 2020-2021 are in Colorado. 

AirBnB is looking for more revenue for themselves so there are certain algorithms that cause your listing to rank towards the top.

What you have to do to your website so that Google will rank you #1 on Google right?

Do you know how much money we are making with SERIOUSLY bad shape hosues in the ARV ranke of $200K?

You need to make it easy for them to find YOU.The ONLY way is to rank an amazingly credible website #1 on Google... do paid marketing like PPC or Youtube, facebook ads.