So if I start with a duplex or a quad as my first property my goal would be to have a net cash flow of $500I intend to use the "BRRRR" (Buy, Rehab, Rent, Refinance, Repeat) method but have never used this strategy before so I still have a lot to learn If I only close on two deals starting in 2019 then I will need to find another 20 deals in the remaining four years (2020-2024) that also meet this criteriaBeyond 2024 I plan to continue to scale even more over the next 3-5 years with an end goal of financial independence by ~2030 (meaning that I will not work a "day job" but will passively manage my real estate portfolio)Biggest hurdle: I'm going to be living outside of the US for the next 3 years and will (likely) not be able to physically see any properties that I plan to purchase.

What did you find was the biggest hurdle getting to closing table?

But if you are trying to maximize your cash flow then a 30 year might be a better option.Some other options to consider...there are "low doc loans" that may require less down if that's your hurdle. 

The strategy would work  better if it were your primary residence, but it becomes more difficult if you're trying to convert a SFH to a true two-tenant duplex.1) You'd must likely be violating zoning (Unless area was zoned MF), so you'd have to hope the conversion flies under the radar.2) Utilities is the biggest hurdle, as a SFH only has one water, electric, and gas meter.

I am playing with the idea of wholesaling if a really low offer is accepted, it would just have to be so low, its almost unreasonable!

The debt is a big hurdle.  

The first house was no doubt the biggest hurdle in getting into real estate, but the current dilemma is "now what"?  

But Randy Richter is an excellent realtor who has helped us purchase our rental houses in Cedar Rapids.The rental inspections are fairly thorough, but not unreasonably picky in my experience.

One of my major remaining hurdles is that I don't yet have a good sense for the reasonable costs of many renovation projects and repairs.

We are stumped as to the legal hurdles though, could someone help point us in the right direction with some of the below questions!