Even on the other forums, when I tell people that I did it by working a 50 hr W2 and using my downtime (nights, weekends, holidays, vacations) to build the business, 95% or more just tune out.

Will cut down trees and poison over the winter. 

One of my cabin's is up on a knob off a mountain in the Smokies so different environment than you but the issues are probably the same and they all revolve around winter, albeit I am guessing yours will be much worse than ours.Mild scenario is where guest are at the cabin and a snow/ice storm hits while they are at the cabin.  

Not looking to rake in millions, but lookign to at least break even as we would be using the property as well in summer and maybe winter here and there.

I think if you can find a $300k house that's a 3x2 that needs a little bit of work and you can have some small equity built up day 1 that might work.I would look in the Apopka, Forest City, Longwood, Casselberry, and Winter Springs areas and try to find a house for around $300k, the rent should be $1700-$2,200 and that might cash flow you a little bit.

@Colt Clark I give $50 off January rent which I hand write in a Holiday card in December to tenants who have paid on time all year or since their lease started.

Whats a good solution for a back yard to be easy to handle in the summer like in the winter? Ive

Read 10 of these before winter break...Buffet, Trump, Bloomberg, Craig Hall, Trammell Crow, Jerry Jones, Michael Dell, Bill Gates, Bezos, Sam Zell, Li Ka-shing, Chuck Feeney, Ong Beng Seng....

Utility bills can increase significantly if guests stay for months during hot summers or cold winters.

In the south suburbs, there are tons of great single-family cosmetic flipsWe do have winter, high taxes, and crime, but like anything else there is pros & cons to everything.