Hello, I am a 21 year old embarking on my journey into real estate, specifically focusing on multi-family properties.

You've made a lot of general statements about Roofstock without specifics. 

I do have a third goal, but too much will happen by the time my second goal materializes that my third goal will likely change drastically.Also, I tend to find myself wanting to ask market-specific questions to agents/lenders/investors/contractors/etc. a lot.

It would be hard to cash flow on a 600k house that has 3600 in rent regardless of the broader economic situation going on in society. i find that when someone says BRRR doesn't work anymore they end up meaning it doesn't work well for the specific types of real estate that they want to buy.

It essentially includes having a buyer for a specific property BEFORE entering  in a contract with a seller.  

2) How well did you ask them specifically HOW they would perform specific tasks?

If you go RBTR, here are a few key criteria I've seen to assure comfort of living and lower vacancy / turnover:- at least 400sqft per tenant and no more than 2 tenants to 1 full bath -excess parking where folks aren't blocking each other in and you're not getting complaints from your neighbors about overtaking the street parking.

If you wish to network or ask specific questions about your local market, you can go to your local real estate forum and discuss with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking 5.

Are you exploring a conventional loan or a loan specifically designed for rentals?

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw.