We have done stuff in the La Pine (Remodeledfrom studs a MFD home), New Construction in Three Rivers (Subdivision was Oregon Water Wonderland 2) and in Sunriver, OR (a remodel). I love the area. However; prices are very high there right now, even in the outlying areas.
I can tell you, Sunriver is 100% set up for STR. They allow guests use of the amenities, etc. with the property owners passes. They also have fractional ownership on condos, etc. so when you see outrageously low prices, that's what it is! It's a great way to get your feet wet, and learn the market there, with less risk.
La Pine is beautiful, but gets a lot more snow than the city of Bend. It's about 30-40 minute drive. There are vacation rentals there, as it's a great area for waterfalls, river, fishing, etc. However; finding cleaners, etc. may be a lot harder.
Are you planning on building yourself? If so, it's an open book test for a contractors license. If you are planning on hiring subs, you'll need to get licensed as a Developer. They're very strict on that, and you'll get fined, even if it's your own job, and you hire subs.
My niece is the top agent in Sunriver area at Berkshire Hathaway, @Christine Larsen. She also handles properties in La Pine, Three Rivers, etc., and would be happy to help educate you on the area. She's the one that found all the properties we did in Bend. Her son in law is a contractor, and can answer construction questions on costs, etc. if you're hiring a contractor.