Lake Front Purchase Opportunity - Worth It?

[Mike Smith]

Hi all,

I have a single-family rental that's worth about 165K (all I do is build equity - not much cash flow). It's a good property - low maintenance and in a decent neighborhood. I owe a bit of money on it but I could net out some dollars that I could use as a down payment on a lake front property that is worth much, much more. If I dropped my net from the sale and rented the lake front property out for what I think I can get ($2,700) I would be about 500-600 cash flow positive before taxes. Sounds like trading up from a cash-flow perspective is a good move.

What I don't have experience with is renting a house on a lake and renting something for ($2,700).  Note: weekly rentals of the lake front property are not allowed. The lake front property is not the nicest layout wise - kind of a tri-level but its 5 bedrooms with a great view and a cove for swimming that isn't out in the boat traffic area).

Anyone have experience renting a place like this on a yearly lease - is that a difficult ask?

Would I have extra insurance costs (tenant would be allowed to have a boat if they want)?

Should I have a tenant sign a special document releasing me if any accidents occur (god forbid a swimming accident should occur)?

Anything else to consider?

Thanks!