I am about to submit to the IRS my log of 500+ hours working in the STR business, most of which come from communicating with guests, cleaners, maintenance people, Airbnb, VRBO, and managing supplies, shopping, bill paying, pricing, calendars, all the daily and weekly tasks. 

On that one, we documented maintenance issues and owner did NOT allow us to repair.

This isn’t really a big deal though.Rent payments can be abated over unresolved maintenance issues and tenants failing to abide by S8 requirements.Many S8 housing commissions will not hold tenants accountable for damages they cause (tenant is supposed to repair or lose their voucher).

If you spend it on unpaid rent or maintenance along the way, you'll deplete your leverage.2.

Ask the manager to explain their process for dealing with maintenance, late rent, evictions, turnover, etc.

Lower-income renters tend to generate significantly higher maintenance and turnover costs.

Your cashflow is decent for the two investment condos and you have reduced maintenance there because of the HOA (but you have HOA which is a hindrance), but I would rather sell those and trade up to a multi with no HOA.

Do you cover items such as lawn maintenance, extermination, alarm and cable services?

@Chris GrenzigYes, the long term tenant’s unit would require a lot of work to turnover. i met him and he seems to be nice and low maintenance so I’d like to keep him in place. 

The cash flow you earn from rentals will likely be best spent on maintenance, unexpected expenses, and reinvesting in future opportunities.