Lots of great folks here! 

But my rental is not generating any cash flow in fact I have to pay for tax and HOA out of my own pocket.  

There is definitely a peak season, the end of May through Labor Day.

I've been a landlord for a little over 2 years and I've learned a lot of stuff, but one of the most annoying lesson's I'm dealing with is that I just can't trust anything tenants say.

If you're worried about the seasonality of the Dells area and filling vacancies during "off times" aka winter.

Saw you were based out of Indiana.. are you thinking about investing in that market or open to other areas as well?

With regard to RE/MAX Haven Property Management, you should know that they are part of the Azzam team. 

The first one that comes to mind is property management.

What’s the most relevant real estate news you have read or heard in the last thirty days?

However, due to it being:1) In the state of California2) A shared home, rather than an outright external property being rented...the default insurance company on offer advised that many carriers are pulling out of CA and that I should go to a local insurance agency.My current insurance for home policy does not offer a "home-sharing endorsement" but only a separate renter's insurance, which would complicate things, since it's for traveling professionals, and they're not going to be booking for 12 straight months.