I am working on getting the exterior painted and one of the units will need a full remodel.

I have REPS by actively and materially participating in my rental property portfolio, and also work as a real estate broker full time (1099 collecting commissions through a single member/purpose LLC) from buildings I sell.My losses from my rental properties (LLC #A) largely offset any federal and state taxes from my brokerage business (LLC #B).

Is it risky to jump into something first time and not know the end result?

Quote from @Tom Grieshammer: I’m 26 and have saved up 120,000 working as a full time teacher and swim coach, so I don’t have a ton of time.

Less oversupply with that product type and more renters that were renting the more expensive bigger cabins are choosing the lesser ones because they love the area but don't want to spend as much on rent.We've talked with several long time investors out there and there isn't a one that have held on to their cabins over time that aren't still adding more. 

Rinse and repeat.It's my first time going through the entire home buying process and it's all a bit overwhelming and daunting.

I wouldn't let the time requirements of a 1031 exchange dominate your thinking at this stage in the market.

If you are looking to be very active and run like Mid or short term rentals yourself, or do flips, then you can, but this does not come without risk. if you are looking to pull money out and put it to work in other real estate so it can appreciate over time so you have a larger base of assets that are paid down or off in the future with some cost now, then I do think that is possible. 10% returns as a passive investor, especially in the first couple years is not likely. 

I'd use a PM unless you were doing this full time and had a portfolio of rentals.

@Mathew Fuller I have not done a flip but have friends that do that full time.