I've been considering joining lately as well and would love to hear some honest feedback on it

However, I think there are some nuances to consider, especially for those still interested in STRs or real estate in general.1.

Not sure your living situation but something I would definitely consider if possible. 

The one thing to consider is that IL and NY are both not landlord friendly states.

You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a tax strategist who is willing to work with you throughout the year, not just when preparing your tax return.

You could start with your agent or a local agent who supports investors and could have contacts to refer to you.Lastly, you could consider negotiating with a local PM to take on a hybrid approach to management.  

It is not an easy thing to run a property when your customers are horrible haha.I recommend student housing with 9 or 10 months lease and run STR during the summer for this property while students are on vacation.

Our actual carriers used to be Secura, but they seem to be getting out of a lot of insurance lines or pricing so high as to have customers drop off, and we just moved policies in Nov. to Hanover Insurance. 

Costs after it’s placed in service are deductible as rental expenses.If you need help tracking these costs or categorizing them for your tax return, consider working with a tax professional or using software that helps you manage rental property expenses.

A net listing is a type of real estate listing agreement where the seller specifies a minimum price they would like to receive from the sale, and any amount over that price is considered the real estate agent's commission.