we have about $400-500k liquid we could use for investing but feels like we missed the boat by 3+ years. 

I came across this post from three years ago, as I'm now in the same boat you were then--Looking for a local accountant!

I'm in the same boat as you.

Your committed to doing this, cross the river and burn the boat committed.

Purchase price: $279,000 Cash invested: $79,000 Beautiful 2 bed/bath condo on a golf course less than a mile from the lake and boat slip.

I have this dream of an STR or MTR locally where I can manage a property with a lakefront myself and go fishing/boating/biking etc when it's not rented.

Hey Alex, yes other people are in your boat.

Khyati Hi Khyati, Cleveland is a great market and I've brokered several deals there for clients in a similar boat looking for higher cash flow. 

@Joel OhA taxpayer renting a "dwelling unit", such as a house, apartment, condominium, mobile home, or boat on a short-term basis, from a single room to the entire property, typically reports the rental activity in their individual tax return on Schedule E.

I guess an earlier start is a common regret, I'm in the same boat.