@Jill KellerI personally owned and managed several rental properties, mainly one family, 3-families and been advised by a number of attorneys through the years to forget doing LLC's.

@Emily CurtisI am a BP Pro Member with login of my personal email I have been using Stessa for 3.5 years using my business email address for login.

From personal experience, this can motivate them to do a final deep clean before handing over the keys.Finally, for peace of mind, you might consider consulting a local real estate attorney.

I don't know a single person who regrets starting out with a quad and house hacking.

@Jesse Streng  It’s definitely important to have a dependable person here in the city.

This is not personal, but if a person cannot save money now real estate is the worst investment to get into as it is one of the most cost intensive businesses to be in.  

Some hotels actually have a condo like structure, where people can own the units, but perhaps are limited on their personal use to only a certain amount of the year - the rest of the year it is in the rental pool managed by the hotel.If numerous room owners stopped paying their bills, you could get tax liens on numerous separately owned units.Hotels are a tough business, an issue I also see come up with them often is that they require refreshes, expensive and relatively often - at least once every 10 years, if not more often. 

You want this to be your backup plan if things take longer than anticipated, you do not want to dip into personal credit cards so i would use a heloc to help with down payment but try to keep a nice available balance on a heloc as your insurance policy. 

The second part is very personal and different for everyone. 

The loan does need to be secured by the property being improved if we are talking about a personal residence and personal itemized deductions on Schedule A.