I've lived in Chicago my entire life and have worked in all the neighborhoods and many of the suburbs, so I love talking about local info with anyone who will listen!

I live in CA and plan to invest into a RE rental property in Florida incorporating business entities for an assets protection. 

Many now getting back to live events.

STRs require a lot more cash up front so you just want to make sure you have a good idea of what you're getting into first :) I own STRs and love it but I also wish I had learned a little more about the analysis and management prior to going live - I did some of that on the back end and could have been successful faster.Another idea is to talk with some owners 1:1 to see what advice they would have for someone starting out.

My goal is to cover monthly housing expenses and then eventually to cover cost of living expenses beyond that by purchasing a few mid term rental properties.

@Suzy Farman my market is so hot I typically only need 2-3 weeks because many people are either living with family or already have a replacement tenant ready for their current unit upon move out.

I have living arrangements covered so I can rent out the 3 bed when I'm done.

It helps you get into real estate with minimal down and allows you to reduce your living expenses.

I have found a good property manager as I live out of state.

*I do not wish to trick my employer or any financial institution, I simply want to take advantage of the 5% multifamily down-payment and flexibility of my corporate job. you need to notify your employer where you are living and adjust your employer taxes as well as each state has different employee/employer laws and benefits.Regarding marking remote or wisconsin, not sure where that comes into play.