You're completely dependent on the quality of your property management company and when they do a poor job screening, you end up with a destroyed property and expensive evictions.

If looking at this correctly, it will place us essentially into the "financial freedom" area we've been striving for (but we will still keep our day jobs).  

I am blessed with great tenants but I still want to sell at market price ($335K-ish) because I lost my job and I am planning to leave the country to find job elsewhere.

Good job Courtney.

Which leads me to my goals in REI - the end goal is to build a rental portfolio that will provide enough income to allow me to quit my job, but I'm not in a place financially just yet to start that.

i would stay away from SFH as your first purchase. you are 100% responsible for that mortgage should something happen like you lose your job or something. a multi family gives you breathing room. one thing to keep in mind is the taxes...sure the Bronx may have higher prices compared to NJ....but you can find properties in the bronx with 2-3k annual property tax rates.....while Jersey has some of the highest property tax rates in the country. factor that into your math and not just the purchase price. 

I was curious if there were any others who started wholesaling part time outside of their 9-5 jobs and found success, or even failure.

I'm from Massachusetts, and I'm specifically interested in land flipping, at least to start - the low barrier to entry, the simplicity (vs rentals), and ability to do it while working a full time job and being a dad makes it appealing to me. 

Your ARV could be less, therefore you cannot pull as much equity out.Your tenants could lose their jobs, hence not being to pay rent on timeIf you have vacancies, it might take longer to rent the unit.

I would be looking for high paying work, side jobs,  sell my things, something.