One needs to have outstanding local market knowledge to underwrite effectively. 

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

Best bet is to try local and credit unions, possibly may have some programs for better rates.

Right now, I’m in full research and networking mode—learning about Milwaukee’s neighborhoods, connecting with local investors, and exploring my first investment.

As U.S. citizens residing in Europe, we are required by the local tax code to hold the property in our personal name.

Return:Finishing the basement and adding bedrooms can add significant value, especially if your local market places a premium on additional living space.

I’m trying to increase my presence to the local renter population.

I am about ready to just manage myself from out of state and have a couple of local handymen help me out when things come up.

To invest out of state successfully, focus on building a strong local team (agent, PM, contractors), automating deal analysis, and using contingencies to protect yourself.

Wrapping 3 properties into one blanket loan shouldn't be a problem, save these are sitting on any sizeable acreage.You might get lucky and find a unicorn local bank or credit union that would consider that kind of leverage, but I would say overall, those terms are very unrealistic.Cheers!