Short term bridge loan, they require much less down payment (10% or less) after stabilizing the units you can refinance with a better loan option.2.

Since it already cash flows, that could ease that burden for you.For funds, I'm not sure what your existing rate and terms are but you could always try a cash out refinance to fund the next property.

Now it's stable, and time to take out the hard money with long term institutional debt.

The house currently rents for $1450/month, we have long-term tenants, and we use a management company.

If you do have to sell in the short-term you might not recoup all the money you put in.

I used to live in northern Illinois, so close to Wisconsin - there are several smaller towns around lakes that would be good for short term rentals. 

Many lenders offer flexible financing terms up to 85% in some instances for investment property transactions. 

You click on the details of the current reservation and scroll down to change reservation.

I'm diving into the world of short term rentals and looking for some advice on the best ways to research local regulations in different towns and cities within a state.

I would try to find a short term/mid term rental friendly agent who might be able to give you super accurate feedback on the market