I'm a pro, and I could not frame it in 3 days, or roof it in 3 hours, nor would I want to, even at a fixed price...tortoise and the hare is my guiding fable. If you could line up a series of crews to show up promptly, have material delivery run like clockwork, good access, flat site, power right there...then you should be able to go from breaking ground to framed, roofed, windows/doors in, plumbing and wiring roughed in, in a couple weeks....for a couple retired guys taking their time, doing everything right, commuting to the jobsite, figure at least 6 to 8 weeks.....factor in the weather too....

Use a ridge BEAM so you don't need to worry about the outward thrust.

Version 1.5.6b - 02.16.2020
- Added the following Simpson column bases to the built-in library: CBSQ44, CBSQ46, CBSQ86, CBSQ88

I realize that this is a complicated question, the answer to which is dependent on numerous variables, but how many man hours would it take to build the 1.5 story cottage? I am a firefighter who bought retirement land 5 hours from where we live, so I can only work on it 1 to 2 weeks at a time. I can do basic framing, but have no experience laying cinder block ( for foundation work) or doing plumbing/electric. There are two retired friends, one of whom is an electrician who built his own house by hand, who are willing to help out frequently.

So, are there any of the following that could reasonably be attempted over the course of 2 weeks.

Foundation (conventional - footers and cinder block)
Framing/ roofing
Plumbing
Electric
Etc.

What’s the best way to go about planning and executing this, given my time and distance limitations?

based on your later answer of 16x30 1.5 story; a wild guess

1 visit for laying block if someone else excavates and does the footing -> a 4' frost depth = 6' stem wall. That will take a lot longer than a 2' frost depth.
2 visits to frame and sheath
1 visit for windows and doors. *maybe* you could get the roofing done too
1 visit for rough plumbing and electrical
1 visit for siding
1 visit for insulation and hanging drywall - or putting up wood paneling
1 visit for mudding and trimwork, finishing electrical; maybe staircase
1 vist for painting drywall or finishing wood paneling
1 visit for bathroom
1 visit for premade kitchen: cabinets; countertop; sink; kitchen plumbing; etc
1 visit for flooring
5+ more visits for random stuff im not thinking about now; like washer dryer install, wood stove or heating/cooling method, dealing with inspectors
5 more visits for when things go wrong; like it rained or delivery was delayed or tools broke, forgotten.. many more things

22 visits x 1.5 week average = 31 weeks @ 50 hours a week = 1550 hours labor

At home you could end up spending 100s or even over a 1000 hours learning how to build. I think I spent at least as much time - or more - researching as I did building. You could even say planning hours = labor hours just to be ready for that possibility.

Just an idea of how to think about it. The more primitive the building the faster it goes together.

Yep lot's of variables. Might be easier if you give a timeframe for being done. A lockable structure or shell is one way to get it going. How safe is the area and is there an option to sub some of it out to get it done faster. Is this going to be a full time home someday? How many square feet? All of these answers will help get you an answer.