They can help you navigate the market and avoid common pitfalls.If you’re serious about taking the plunge, start analyzing properties in both Boston and Chicago markets to understand local trends.

(It doesn’t pay its own taxes.

I do not want to stretch into California due to the Landlord laws and taxes. 

Do the tax benefits make it a good deal?

Working with Real Estate ProfessionalsLocal Real Estate Agent: Choose an agent experienced in student housing.Property Management Services: Consider hiring a property manager if you’re not local.Inspection and Appraisal: Conduct thorough due diligence to avoid costly repairs.6.

Are there issues that you think you should avoid regardless of potential for discount? 

If you have siblings on the deed, that starting number from an appraisal is one you will need for tax purposes going forward.

In Berlin, rental arbitrage has been very profitable, with average annual margins of 25-40% after all costs but before taxes, so shifting to a market where arbitrage is barely breaking even is definitely a reality check.Given your experience, would you say the best way to enter the market now is through purchasing properties with financing?

a lot of people will poo poo this, but I also live in a market where cash flow is low, property taxes are high and properties are expensive (which is a relative term).

Malibu allows it but requires a 15% "hotel tax" on the gross revenue.I would recommend looking out of state or underwrite the property as a long term rental in the event laws change.