I'm a big believer in the economies of scale and would like to focus on Multifamily Properties, specifically apartment buildings 5-16 units.

The City Planning Commission last met March 12, 2019 and voted to limit short-term rentals in residential areas to owner-occupied properties, sending the proposal to the City Council for a final decision.The plan forwarded by the council would also place some additional limits on properties in residential areas that are zoned for mixed-use, multi-family or commercial uses, treating them the same as traditional bed-and-breakfasts and making them subject to a restriction that limits them to one per side of a block.Under the commission's recommendations, large-scale short-term rental operations would be allowed in commercial districts such as the Central Business District, the neighborhood that currently has the highest number of licenses.

It's how I got my start (with 1 property) and now up to 20 total doors (and scaling).  

I don't know how much money you have, but using OPM allows you to scale much faster than tying up all of your own money in a single deal, etc.   

In general they will be pricier and less experienced because they do not have economies of scale and depth of experience. 

After having to file for eviction numerious times, we were able to get the owner to agree to down scale from operation three units to only occupying one unit.

It's a great way to gain experience and decide if being a landlord is something you'll want to do on a larger scale.

At scale, vet all parties. 

I'm starting to realize that it will be easier to scale up with other investors working with me. 

The company that owned that lot paid me to mow it while I mowed mine but I doubt that I'd start my own larger scale lawn care business.