(Hint - go on VRBO and see what your local competition is charging). 2) How much do you intend to put down?

I found this deal as an off-market property through my local network in the Hamptons.

As others said out of state can be more challenging based on location but local or out of state both can be done. 

Howdy,I haven't decided if we are gonna manage the property or hire a local area property manager yet.

Are there any local meet ups or websites on where to find more people who have a moderate level of experience meaning they are  somewhat experienced but still looking to collaborate and network with more inexperienced investors like myself.

I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.

Networking with Canadians who’ve invested in the U.S. and finding good local agents or property managers will also help a lot.

I agree local banks and credit unions will be better if you're planning on growing your portfolio. 

Look for distressed properties through online platforms or local agents.

I personally think it is best to work with local professionals with a good track record.