If he files a transfer deed to the Land Trust or if he "sells it" then property taxes increase, the change in hazard insurance becomes a tangle.I wouldn't give authority to a bank person to collect rents, file evictions, deal with repairs... there are set up costs and on-going management costs.

If at least one person is going to be working from home, an office setup may be desirable, although a lot of people prefer not to be glued to a desk and like to move around the home as they work.

Depending on how you set up your STR that could affect you.

Companies are unlikely to set up new operations in cities with high crime or high overhead costs.

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

@Alicia MarksCan you set up a forum and investing program for active military personnel?  

You can also set up Monday boards that are shared among multiple people so you can see each others notes.

Hadn't set up an account with the gas company either.

Buildium and Appfolio seem more expensive, but I have setup calls with account managers with both.

My current CPA is not well versed in the realm of short term rentals, finding one that is has been on my pipeline but with all the work involved with the property setup I haven’t gotten around to it.