Total rents at 100% occupancy across the three are $2900 monthly.I'm thinking because the financing terms are soooo attractive that it may be worth the higher risk that comes with the high PITI?

Its going to be more about those factors than any local market factors for DSCR Lenders.The lender should have gone over the prepayment provisions more closely before closing, but assuming you likely have whats called a "stepdown" prepayment penalty shorthand called "5/4/3/2/1" - this means that you can refinance and prepay, however if done in the first year of term you will have to pay a 5% fee, second year 4%, third year 3% etc. 

Make sure the $400-$500/month cash flow is enough to cover unexpected costs.It wouldn't hurt to look for other refi options or consider a different loan option, which might offer better terms.

While discussing terms with buyer the topic of which agent will I be using come up.

I'm thinking one might be that it wouldn't show established long-term tenancy in the case that I may want/need to for lending purposes. 

Hey everyone,I’ve got a friend who own’s a very large home with a pool, and is trying to find someone who can be her short term rental manager.

In November I submitted my shared-housing application to Chicago’s BACP, with the hopes using my basement unit as a short term rental unit (Airbnb, VRBO, FF, etc.). 

They will handle all aspects of renting out your second home.Long-Term Rentals (LTR): The management firm can find long-term tenants for your property, screen potential renters, handle lease agreements, and manage any issues that arise during the tenancy.Seasonal or Short-Term Rentals: If you prefer to rent out your property on a seasonal or short-term basis, the management firm can handle marketing, bookings, check-ins, check-outs, and cleaning between guests.

There is nothing simple here.

However, clarifying the long-term business objectives/strategy is key before finalizing your entity set-up.