Sellers haven't quite realized this yet and are living in the rosy rate climate of 18 months ago.

$700 for snow removal is criminal...in this climate snow removal is always a tenants requirement for properties under 5-units...all costs should be passed back to your tenants (within reason)...I would suggest finding a new company with a percentage-based approach...you should be paying 8-10% of gross income and your operating expenses should be declining year-after-year...on managed properties our goal is to get operating expenses to 20% of gross income or lower...and that is mostly routine repairs and preventive maintenance...Once the property is stable, operations go on auto-pilot...the biggest concern should be budgeting for upcoming improvements, capex and repairs

Class B (second generation, mid size, suburban, drive up, may include climate control)  equal to a Blue Chip stock. 

The climate cooling hysteria was well...hysterical....

In terms of locale, one thing I've not read about in the comments is climate change.

The climate was amazing...

Significant cost factors include: property taxes, insurance costs, state income taxes, property age and construction, climate, and eviction cost and time.

Especially the smaller STRs -- the big resorts have been slower recently, although the political climate may have something to do with that (11-12/2020)Clearwater and Clearwater Beach are no-go for STR unless you buy in a condo-hotel, or really lik eplaying with fire. 

Easier said then done I know, but you'll get a much higher, and faster, ROI getting a raise compared to putting 100K into something that net's a few hundred in cash flow a month for example.Your idea of 4-5 paid off properties sounds great based off of today's climate, but it won't sustain you your entire life.

Whats the cities political climate?