Of course we all have to start somewhere but I tell everyone I do business with regardless if it's with me or someone else I always recommend them to build a portfolio.

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 need some recommendations on where to buy the suppliers to STRs, for example paper towels?

., property management companies aren’t legally required to carry general liability insurance, but it’s highly recommended for protection against bodily injury or property damage claims.

Based on the info in your post, my recommendation would be to turn these assets into well oiled machines and max out their NOI.

build to rent is great. they are an intermediary that help investors contract direct with turn key new build. they are pretty sophisticated we have sold a house so far and we are looking to sell other multifamily with them. there is a vetting process and as an intermediary they don't control construction they help vet builders and establish relationships. they have a big team. the other builder I've never heard of but unless you can see your house I wouldn't touch it. rent to retirement has a strict policy of 90 days until certificate of occupancy until they will send a deal out they are good at what they do and I'd recommend them. they have options all over the country and established relationships.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I recommend beginning with a turnkey property.

I would also recommend increasing your liability coverage to at least $2M.

Would definitely recommend finding a partner who can help walk you through this if you decide to move ahead.