However, on the contractor's end, it seems they literally stop working depending on the weather, since they are primarily a snow removal company.

unfortunately  the warm weather period is the best time to get a pulse of the neighborhood. 

Just consider the setbacks on starting in REI for the first time and determine if you’re able to weather those.

If you buy right and aren't stretched thin, you can weather the storm.

Preference to the beach as more people tend to travel where the warm weather is vs snow.

Since then, the tenant went to jail, and the payment didn't get made and now their children moved out, cancelled all utilities (shut off) and we have frozen pipes and lots of weather related damage. 

I am doing a ground up build of 2 townhouses. We dug the foundation, the pad was all set to go, the exact correct elevation, etc... and then it rained like crazy for the better part of a month and now the whole site...

I find myself on the fence weather or not I'm big enough to hire my own full time handyman.

Take an air compressor and generator,  put the generator outdoors, hook up the compressor to the boiler, turn compressor on and listen for air rushing out of any breaks. 

Wondering if I will have any resistance to paying through an APP