In addition, if you're actively flipping properties in the area, I currently have time on my hands and I'd be happy to support you in one of your projects in exchange for learning in depth about the process. 

If you are open to it, I'd be happy to share more about why these locations are so promising.

For background, I'm partnered with an architect and interior designer, but I'd have to find most of the subs as I don't have any formal connections (at least in the area I'd like to build).

That property was also supposed to be a few month flip, but I had to fire my contractor who I'd been working with on all my properties.

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’d be happy to share some referrals and insights if you’re interested.

I'd be happy to add you to it as well so you could receive weekly snapshots. 

If it was me, I'd look at it this way:1) Paperwork: I can hire an attorney at an hourly rate to write up a purchase contract, etc. 

I'd love to connect and always free to answer any questions! 

Since generally the benefit of a house hack is to hold the primary residence loan as long as possible, if you hold it long-term, you could still be forced to pay the mortgage insurance 10+ years down the line.Plus, you can only have one FHA loan (with some exceptions) at a time, so I'd rather use this house hack for 5% down which I can repeat and save FHA for another time.