I feel like 20-something y/o's are being dupped into it as well, and want to avoid that regret of throwing money in there just because every traditional W-2 employee thinks it's the holy grail for retirement.The reason why I leaned towards not using their plan is:- I plan on retiring by 40 and imagine there's a big penalty for taking money out before 60.

A lot of contractors are crude, imagine dealing with them when you have problems in a project.Visit a current worksite, talk to past clients, don’t just look at pictures of their work, and if you have construction knowledge ask them what they’d to in a hypothetical, make them talk out their process for your project, question their process.

Can you imagine asking 100 people on the street? 

I can imagine that you could have serious issues if it's an illegally converted fourplex.

If this is the way you want to go, I’d suggest you find an investor friendly agent in the market where you want to begin and have him/her start feeding you listings by email.

(His deal structure didn’t happen as I will mention later, emails attached in link, start from the bottom)Emails and Property Financials I left that meeting very confused, to get this deal done I needed to pledge everything I owned and have built to get this deal done.

I start emailing...

Last night after a long day of work and trying to buy a couple Christmas gifts for the kids (I am so behind) I got emailing/texting my property manager about an idea to leverage some staging I did at my apartments into a full on furnished corporate rental option....simultaneously I was emailing back and forth with my contractor about our rehab project....while simultaneously updating my website, tracking invoices, preparing financials for my CPA....and eventually at 12:30am I threw in the towel on getting up at 5am to get my run in (also training for my 23rd marathon).  

I know many, feel free to message me for their email and website info.

As an insurance agent the liability is extremely high and I can't imagine finding any policies that would make it financially feasible.Local municipalities also have regulations regarding short term rentals so that could be another hurdle depending on your city/state/HOA/etc.