I have lived here for nearly 20 years, and the city is segmented into very understandable sections. 

Definitely not attracting crime..How can they be high end if they are (tiny), the high end segment seems to want uniqueness and showy, tiny = poverty...Who is your target market....Mercedes E drivers wish they had an S....but won't (or can't) spend for it.Who is the target market, or is it if you build it they will come?

I talk about my experience starting up on the BP Podcast: Show 25 - My segment comes on around 48 minutes.

My research led me to break down the market of property management software into two main segments.

I am not familiar with the area but the important things to check are STR performance in the area you are looking at as well as the traveler segment you will be targeting (budget, business, family, etc); STR regulations imposed by local authority, county, state; neighborhood sentiment about STRs

Small towns may rely too much on a single business or market segment.

Because the tenant segment willing and able to rent a particular property is fixed, there is little you can do to change this.Property and Tenant Segment RelationshipEach tenant segment has specific housing requirements, and will only rent a property that meets all of their requirements.

Do you recommend to buy in vicinity of 100K in a so-so area where the profit margins are greater but the risks are bigger too or maybe move into the higher segment (say close to 150-200k) where it is probably more stable?

What I'm seeing in practical terms is that this really doesn't matter for my market segment, long-term C'class SFR.

The segment we are trying to hit is people who would normally be staying in a hotel, looking for comparable accommodations without having to spend $300+ per night.