So much so that we’re thinking of buying a place of our own to rent out and stay when we want to.

Mario, instead of focusing on "20 properties" I would buy fewer but better properties.

-"analysis paralysis" is mostly a made up nonsense phrase intended to get people to go ahead and buy real estate even if they aren't ready to do so. 

Instead of just buying into a training/coaching program for $8000, (That is what cost as of yesterday) they have a bank and financing available to the group that seems to be unique. 

I’d recommend waiting till you have a cushion of some sort depending on your comfort level before you take the plunge and buy the second deal.

He is on the market to buy and has expressed interest in our rental.

Quote from @Lee Banks: Hi my name is Lee I'm looking too buy my first rental property and but I feel as if I need a mentor to watch, I still need to learn the basics of real-estate does anyone in New York do programs or mentorships and where would you start if you first started real-estate today  Hello Lee,I'd recommend looking up local meetups here on BP, meetup.com and, eventbrite.You can also call around to speak with RE investors and professionals in your target market to begin making connections.With so much available information online, I'd recommend speaking to a few people and doing independent research before committing to mentorships.

That does not work and is only for experienced renovators who know their buy box and know they will always go to the studs and redo everything.Just get out in the field, see every dump on the market, take sneak photos to show to a contractor, and get some investor and contractor friends who will be in the ballpark on the costs.Understood, Thank you very much!

House hacking is often promoted as the easiest way to get into real estate—buy a property, rent out part of it, and let tenants cover your mortgage.

Better to lose $400 than buy a bad deal