The real play is to get a seller-financed note and then sell all the homes during the term they give you and then refi out.

I am planning to start a direct booking site for my short-term rentals.

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. 

If you do not understand how NOI and cap rate determine value, learn it even if in theory it only applies to commercial RE.If you flip, you realize the gain in the short term.  

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. 

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.

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.). 

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.

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.

But in terms of cash flow I like this more than an EV charger or renovation.