Dealing with non-paying tenants in a state like Massachusetts, which has strong tenant protections, is no small task.

It sounds like the agent you worked with may not have been acting in your best interest, and I would strongly recommend finding another agent.

To invest out of state successfully, focus on building a strong local team (agent, PM, contractors), automating deal analysis, and using contingencies to protect yourself.

Hi BP Family "I’m working on a 15-unit multi-family deal with strong rental & value-add potential.

@Preet Oberoi,I would strongly recommend that you look to partner with someone who has experience in this. 

Start by researching affordable states with strong rental markets and landlord-friendly laws.

In suburban Chicago, historical significance or celebrity ties might create a niche appeal, but they won’t necessarily drive up the home’s market value in the same way as location, condition, and local comps.For a short-term rental, though, it could be a great marketing angle—especially if the person is well-known and has a strong local connection.

Since it sounds like you have strong W2 income and would probably be okay paying the mortgage sometimes, I'd even explore a 5-10% down payment option.

., known for its upscale appeal and strong demand for vacation homes.Properties in the Hamptons attract affluent buyers and renters, offering a high potential for appreciation and steady rental income.he property may have been undervalued due to its condition, presenting an opportunity to add value through targeted renovations.

I find it a great way to earn additional compensation as long as its a deal I like with conservative leverage and strong operators I trust.