@Michael HigginsThey make money by doing an honest assessment of what the property needs and deciding how much they could pay for the property and still achieve their goals.

But a dozen paid off properties mostly with property management is stress free and more than we need. 

Not as comfortable assessing the market. 

Then, because my friends and family wanted to invest alongside me, I started to explore syndications and have been able to co-sponsor dozens of large-scale multifamily deals across the country.

I agree with your assessment and will continue to assess the situation. 

Special assessments can be real killers.

Let's possibly talk about the intuitional hedge funds that are backed by billions that buy up homes by the dozen at whatever price because they can, before we worry about the average STR (which is still primarily owned by the little guy's and girl's) and other rental owners. 

In between tenants, you may ned to go out there to property assess the condition of the place to refund the securty deposit, but you can do it yourself if you are knowledgable about the laws, etc. 

I'm looking to purchase my first rental property (second mortgage); However, on confirming with our bank, they do not consider future rental income from the property on their assessment.

By comparing what you can observe about the condition of many elements, with what the planned schedule is for that element, you can get an idea of what is having maintenance deferred, and what is being well maintained.There should also be calculations that show the percentage of funding they are planning, which should be well above 65% to ensure no unexpected maintenance fee increases or special assessments.