Just realize you do need to learn to operate the LLC property to maintain its corporate veil.. 

Digital nomads, corporate travelers, construction workers, relocations, families experiencing an insurance claim and many, many more types of travelers are looking for furnished accommodations and they each have different requirements for what they're looking for.

I'm interested in setting up either an S-CORP or LLC, but want to make sure i make the right choice so that I can secure the best tax benefits, while also setting myself up to get into the next investment. 

@Robert RixerI'm not one to upvote an argument based on the thinking of Blackstone (I think corporate's amassing of real estate is a real problem for America), but the idea is nonetheless a good one. 

Check out the Neighborhood Assistance Corporation of America (NACA).NACA was formed in 1988 and provides an affordable option for potential first-time buyers:✅ No down payment✅ No closing costs or fees✅ No mortgage insurance✅ No consideration of credit score✅ Below market fixed interest rateThere are several requirements to be eligible, starting with attending one of their workshops.https://www.naca.com

Before purchasing, I would make sure to figure out your area's vacancy rate and figure out what the largest corporations are that offer housing to their employees are.

Should the holding company be an S corp or LLC??

There are a plethora of attorneys on BP feel so free to do a search for corporate attorneys and choose one that can assist with properly structuring your LLCs. 

I made more on two flips in a year than at my Full Time CORPORATE Job.

I was also concerned if would compromise the corporate veil if initially was in my name then switched to an LLC even with a separate account and everything....