Sub 2 was not in my vocabulary 3 years ago when I started in Real Estate, now Sub 2 or buying subject to its existing financing is a common term I use daily!

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. 

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?

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 am planning to get my first investment house; I don't want to use my savings, so I have an equity line of credit for 50K and got pre-approved for a loan up to 300 k? 

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. 

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.