If you can get a single family home and have roommates, that's the most approachable strategy and will really allow you to know rather quickly if you hate managing rentals or not.Here's my experience starting at 22, and what I regretted from house hacking: https://www.biggerpockets.com/forums/922/topics/1133476-hous... 

You might want to ask these questions in the General Landlording https://www.biggerpockets.com/forums/52 or the Medium Term Rental forum, https://www.biggerpockets.com/forums/925 which is what you're doing if they are furnished rooms. 

Here are some coming on BP: https://www.biggerpockets.com/forums/521-real-estate-events-...We have a list of a lot more investor meetups that I will happily share with you. 

We do not verify identities, that would be a bigger lift than we are capable of currently, however it is against the rules to use a false identity per section 2.A of our website rules here https://www.biggerpockets.com/rulesSo anyone discovered using a false identity will be removed if they are reported to spam.

The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

Once you feel you've built a strong team with your first property and have solid systems in place, I would then start buying more aggressively and taking on bigger projects.I suggest reading this BP article on the core 4.https://www.biggerpockets.com/blog/core-four-real-estate-team

Personally, i would be cautious telling the majority of experienced owners/hosts they are wrong without rock solid data and evidence.https://www.biggerpockets.com/forums/530/topics/1155394-have...https://www.biggerpockets.com/forums/530/topics/1155264-afte... 

The most important thing is to know the details of your local program like the back of your hand, then look for loopholes.Just to give you and the other BP'ers a deeper handle on why some TDR programs work and some don't, I just uploaded an excellent study on the topic to my FilePlace at http://www.biggerpockets.com/files/user/ChrisNewma...

Since the properties are in New York you have a few extra steps you need to do to keep all of your funds out of NYs hands at closing.Here's an interesting BP thread on the South Carolina property tax issue you mentioned. https://www.biggerpockets.com/forums/725/topics/604427-south.... 

Most operators post on multiple STR OTAshttps://www.biggerpockets.com/airbnb-calculatorGood luck