I'm getting to a point where I might want to pursue a lender for future investments but am trying to understand how these lenders choose people to work with. 

It really depends on your market and the owner's needs if sub to is even possible.

Also, more people seem to be choosing trade schools over traditional colleges.

I respect your many years of experience Jay but want to bring some perspective from the other side of the table.In a corporate office which is running 10, 20 or even 50 projects at once (depending on the firm size), what is the benefit for the Architect to drop their other projects to jump on yours quicker?

I also find that depending on the tenant, my one Airbnb property has less wear and tear because it's constantly cleaned and maintained versus my other rentals where the families living there settle in and accumulate stuff - which makes it hard to deep clean regularly (to my liking) as well as just the constant daily wear and tear from kids etc. 

There's no right or wrong way to do this, just varying levels of risk and reward and YOU need to understand what they are for whatever strategy you choose. 

Depending on when the STR was placed-into-service, depreciation will be prorated based on the amount of months remaining the tax year. 

@Ella VolneyTypically, you can only find a lender in the country where the property is located and, if you're not a resident there, it will be more difficult if not impossible, depending on the country.When it comes to investors, they need to be open to the idea and then you need to have opportunities that fit within their right risk/return profile.

Highly depends on the particular community. 

It just depends what you are looking for though.