Bigger Pockets is a great place for education and networking and is full of great content.I recommend that you check out the following resources:1.

@Michael Whitman very good point and something to check on ahead of taking the loan.

It's a good idea to schedule your own safety inspections, including checking for smoke detectors and carbon monoxide alarms.3.

If you have a swimming pool check out the water pump system with aerial hoses.  

Quote from @John Warren: @Delroy Watson I would check to see if you can do this the "right" way and make it an ADU.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Im not an STR SME - I would check with Mike Savage and Dan Rivers - theyre the local experts on STRs.

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).

The IRS doesn't trust you to report accurate information, so the 1099 from the property manager is checked against your filing.Any company that does more than $600 in business with you should issue a 1099.

Had a quick question.I purchased the property for $500K about 10 years agoI'm selling the property for $575K with the Fire DamageI received an insurance check of $380K for the fire damage.After Paying off the Mortgage + Escrow + Realtor Fee's, I'll be left with about $150K.My question is will I get taxed on this $150K?