I'd love to hear about your experiences—what works, what doesn't, and any tips for making remote property management easier.

But if you're living on site and knocking on doors to collect rent, could work out for you. 

This could be anything from confusing UX to lack of certain integrations.How useful would a custom listing site be for you?

IF it is skiers are you providing good resources for ski delivery, transportation, tips and tricks for parking, deals on lift tickets, etc.

I am looking for any tips on how to structure my LLC as well as the best cities for Ohio.

Check out the exceptions to the law as it does not apply to all rentals:https://www.nyc.gov/site/hpd/services-and-information/good-c...If it did apply to you, month-to-month agreements would still allow you to do rent increases any time.

Any suggestions and tips?

@Justin,  No you don't need to provide notice however make sure to notify if you will be disturbing common areas, shutting off water to washing machines, having alot of workmen on site. 

Any tips for building a solid list?

You need to amass a large portfolio for it to be passive (aka hiring someone to manage).If you want to be financially independent as fast as you can then you need to do a few things. 1) get as high of an income as possible (this usually takes schooling and/or experience, think high income profession - law, medicine,etc)2) live as frugally as possible (you will sacrifice a lot here, think of not going out with friends, live at home/save on rent, etc)3) invest as much as possible and I mean invest not yoloing on random hot tips (you are starting young, time will be on your side)If you do this consistently and remain highly disciplined, you will get there faster than most.