But I'm starting to wonder if and when some appreciation resumes, and if and when market will dictate rent increases.Appreciate any opinions - thanks

Welcome to BP @Shai Shushan You started in a great place! 

Congrats on starting your short-term rental journey!

@Andy Ptak when jumping into the industry you have a few choices:1) Start at the bottom2) Leverage your experience to convince someone to give you a chance3) Decide between:--- Big companies who will usually start you at the bottom--- Small companies that will more like to a chance on hiring you for an above entry level position.

How do I even start the conversation as a tenant?

You have started your journey in the right place.

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Over time your Tampa investment will start to cash flow.

It's a new suburb just starting out ,there are no large single family rentals ,it's mostly townhomes that are being rented out, which falls in 2500-2700$ .