My initial plan had been to do something like Rent-to-Retirement or REI Nation- assuming that I'd be leaving money on the table to pay for their expertise, but hoping that I would learn through the process and develop the confidence to strike out on my own later. 

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 love to connect more directly in the near future.

I was thinking this might work on my property in Redding and can be adapted to a shared housing project for seniors (though I'd want rooms large enough for bed, bath and seating area)  It's my understanding that it is considered a SFR with seperated bedrooms as far as planning.

I'd weigh lightly on the 'trust' aspect.  

IT looks beautiful, I can only imagine the satisfaction you must have felt putting on that final coat of paint and saying "finally". 

I imagine some may have a better view, more bedrooms, or more amenities. 

If you have any advice for someone just getting started, I’d love to hear it!

I'd talk to more contractors on how to solve the problem.

I realize people are trying to make a living, but anyone who cold calls me is the last person I'd use for any transaction (plus I have people for that!).