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).

What broker would sponsor me considering I'm not intending to become a full time Realtor and give them regular business?

2. have you noticed higher and regular exterior maintence protection (sealing/weatherproofing/termite/bug protection) or anythign?

In addition to a voucher, we require that the tenant be able to show income at least 1.5 time the monthly rent, as opposed to our regular tenants who must show 3.5 time monthly rent.

I also actively invest in real estate myself, and I talk with investors regularly about how they evaluate deals.Out of curiosity, what key metrics do you use to decide whether a deal is worth pursuing?

If you buy regular keyed locks (non-electronic) as Nathan Gesner recommended, then buy Schlage because they have a lifetime warranty on mechanical and finish. 

could be just like a regular deal, but if you're up for pitching, presenting and educating a seller on the tax and other advantages of seller financing, you just might turn it into a seller finance deal.

Regular progress meetings and budget reviews will help you stay on track.Wishing you success with your development!

Start with maintenance notes that you may regularly reference, such as air filter size, water shut-off location, etc.

Is the property just a regular-style house or something you can build an experience around?