I suppose you have been reporting the rental income and expenses(including depreciation) on your tax return.If you get paid in Italian currency - it is your job to convert the amounts in USD when reporting it on your return.If you hold the property in an entity(partnership or corporation) you may have additional informational forms to file with the IRS.If you have a bank account in Italy with a value over $10,000 - you also have an additional informational forms to file with the IRS.You should have been entitled to a step-up in basis upon inheritance.

This isn't legal advice, and I don't have a real-world example, but some coverage issues to pay attention to might include injuries to common law employees, injuries involving liquor, and punitive damages for gross negligence.Keep in mind that umbrella insurance policies are negotiated contracts like any other insurance policy.

What’s the most common way to keep track of your properties without hiring a professional acocuntant or manager?

@Chris Seveney Question for REOs, Is it common for banks to purchase at the auction and then re-auction the property rather than placing it on the MLS or the HUD?

HELOCs are supposed to close within four to eight weeks but can take longer if underwriting requires additional information or documentation. 

You have equity in your primary residence, so refinancing could be an option to obtain the additional funds needed.

You can then bill additional fees/utilities, etc as needed.

. $1200 is expensive when you consider the alternative that I am suggesting is infinitely expandable at no additional costs for the rest of your life.

If you are considering a larger multi-family, there would be additional things to check like employee records, reserve funds, review of bank accounts, environmental assessment, and more.

If its a normal expense that you would or could have in any year, then we cant add it back as income and those will affect your DTI.