I haven’t had trouble finding tenants in fact I usually have plenty of applicants to choose from except during winter months so I definitely try to avoid filling units in the winter (Oct-April is much harder to find quality applicants).

We’re looking to buying in winter garden, Clermont area.

If you don't I wouldn't wait too much longer as winter approaches.

I’m partial to Breckinridge and know it is a very well-established, heavily visited vacation area but because of that I know the cost to buy in is very high so I’m open to exploring other vacation areas that may be better investments such as Winter Park, Estes Park, Keystone, or any others that I may not be as familiar with.

I say this because everyone is going to be 5x more careful than the normal fall and winter.

Market is strong due to retirees from elsewhere in Canada wanting to have warmer winters.

.), that we would enjoy in the summer half of the year and then rent to snowbirds during the winter half of the year.

Iowa where I am is a good market, but it can be tough to try and do the remote purchase when so many factors such as harsh winters require a little bit of local knowledge.

Property management would not let me paint exterior or leave decorations past the holiday event.

If you're worried about lake rentals this is what I do for winter months.