We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

I think my personal guideline will be 10 properties, or $2k in cash flow a month.

We actually do a real estate investor meetup on the first Saturday of the month in Kihei at South Maui Gardens.

Did you go the DSCR route for the refi or did you wait 12 months to do conventional?

The nice thing about the arbitrage business model, is the companies usually pay you a monthly rent, and then they handle all of the AirBNB stuff. 

Just like how Johnson & Johnson or Coca-Cola send you quarterly dividend checks, your tenants are sending you monthly "dividends" in the form of rent.

I would just get clear on your goals and make sure you have the time in the 6 months to put the lessons learned into action.I would also be happy to connect if you want to know more. 

A manager will roughly cost $100-$150 a month to take over a unit (it could be more or less in your market) and manage the units.

It just came out this month and will hit every question you have about that in my opinion.

Does the bank let you get 2.5 months late on your mortgage payments?