STR path to long term goal of 10+acres?

[Benjamin Frank]

Hello! Our long term goal (one of them) is a 10+ acre, single family, multi-bedroom house/cabin with room for expansion in central-northern Vermont within 30 minutes of skiing to be used as a family vacation home along with STR. We want to begin the journey this year but will likely have ~40k for a down payment. More than anything, monthly payments cause us concern. We don't want to end up with a monthly payment that we couldn't handle if there were long periods of time without renters. We have no previous experience with renting of any kind.

Question: would it be advisable to start with a studio or 1br condo that's within 15 minutes of the slopes, on which we could make monthly payments if we had to and build equity and then trade up in a few years or go right for what we want now and be prepared to work like heck to book it year round? The price difference seems to roughly be 200k vs 500k based on what I've looked at.

What do you do if all of a sudden you can't swing your monthly payments?