I'm not too familiar with Section 8 in Clevland, but if you're ever looking to expand over to PA/Pittsburgh area feel free to reach out!

Could you share your experiences if you have encountered a similar situation?

Happy to connect and share my experience on the ground.

Communication and Management:What are the best ways to communicate with and manage tenants to ensure a positive living experience for everyone?

Hello,I have been reading through the Bigger Pockets Forums to hunt for your good and bad experiences with DSCR Lenders. 

Ideally, I would like to buy in the Catskills since it’s close by, a popular year round destination from the city and has a history of vacation rentals but I know there’s more and more talks of regulations so I am open to other areas and would love to hear your thoughts/experience on the area.Would love to connect with anyone who has interest in the area and the short term world as well as agents familiar with STR who could help us in our search.

In my limited experience, they add no real value to the process, and like you said, don't really know costs, and while ARV is fairly easy to determine, they are always aggressive on those, too.So, how do you not get taken to the cleaner?  

I would love to continue to flip houses but now having two little boys makes the "live-in" part a little difficult.Outside of real estate and taxes, I enjoy spending time with my family, whether at the beach or in the backyard, and sharing new experiences with my 2 sons. 

People staying for just a few months want to experience what that city has to offer.

You will get a better rate and terms, experience, and a faster closing going wholesale than you would going with a retail lender.