Then clear a pool below a spring and rock formation. 

Table 1-4 is the Rollover Chart in IRS Publication 590 that can guide you.

@Andrew Steffens the pool of buyers that have six figures of cash (you really need about $150k in cash to buy a $500k STR), have some subject matter expertise, AND want to self manage is even smaller. 

To win the STR game, especially if you're a new entrant, the most important aspects are 1) Amenities2) Location3) Property type4) UniquenessAll are geared toward you standing out on Airbnb/VRBOHot tubs, fire pit, bowling alley, pools etc. or being in the best location in an area as well as being to host a large group are all things to help you win.

The tenant pool can be lower end in Winnipeg but if you invest in the right areas it will often qualify for CMHC financing in terms of affordability. 

Here in FL that is typically the pool and backyard area. 

Many OOS investors set themselves up for failure because they don't invest the time to ACTUALLY 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.Class A is relatively easy to manage, can even be DIY remote managed from another state.

They come in with a different name usually acquired by buying out a small/mid company, wipe the market with unlimited funds backed by fed and big banks, dry the pool and leave when there is nothing left. 

They have no problem with in ground pools.

No reason not to use a top platform.Regarding the friends thing, that is dirty pool IMHO.