A contractor left a back door open one day and someone walked into the house and stole $2000 worth of tools.

Hey @Brett Baker, generally, any place with a great water view or directly on the water will bring more revenue.Of course profitability will all be based on purchase price and prevailing nightly rates in the area.If you find a cool 2/2 or 3/2 right on the water with a great view for 1.5m or a 2/2 or 3/2 house a block away for 600k, then I would look at the house over the condo.

Another option is house hacking—buying a small multi-unit, living in one, and renting the rest to cut costs.

house hack is possible. base way to get feet wet

Thankfully we are commercial bank clients so our rates are as low as you can get in the market place for anyone who is not Lennar or DR horton or those types.Do you pre-sell houses without hedging a percentage of the supply?  

Not familiar with those markets, but here is my experience starting at 22 and what I regret after house hacking twice: https://www.biggerpockets.com/forums/922/topics/1133476-hous...

You are considering putting a tiny home on your existing property as an ADU or using that money to save up and buy the next investment property and wondering which would be the wiser choice.I think ADUs can help provide additional, much needed, housing.

Consider financing options like hard money loans, or FHA loans for house hacking, and focus on areas with strong rental demand near the MA/NH border.

If you are just getting started here in Chicago, house hacking is the ideal situation.

I buy houses!