Would it be a good idea to take a deposit to secure the deal until the rule clears?

Some other ideas that we're considering to get access to more deals to to try send our flyers and start going to auctions. 

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).

You have an STR listed on the Airbnb platform.Why not look at the design of highly sucessful STR'S in your area and copy some of the best ideas?

It sounds like a great idea!  

My office is in Carmel.  

same with us, we study infill every day though through case examples. the best part about infill is no risk. buying lots like what builders are doing even national builders still are shifting the risk to local land developers. my recommendation is to look at permitted uses, price per acre, etc. if you want lower risk buy a larger tract of land from a large developer out of a 100+ acre development to lower the risk. if you are doing it from scratch work with a group who's doing subdivisions. you can go and read the subdivision plats in your recorders office online every county has one. in columbus where I do the majority of our development we are specifically starting to target zones where the economics are also favorable.

About my ideas and general questions.

Would this be a good idea or even possible?

We always advise our investors on verifying with the lender or us reaching out to the tax assessor's office to get a good idea of what the taxes are.