And if so, should I do so sooner or later?

Which being one of your first flips/investments in the area, you probably are wanting to "realize" the profit from your investment sooner than later.

Some deals are simply dead and the sooner an investor realizes that the better. 

You'll also need to have several years of consistent commission income before being able to qualify for loans, as opposed to a high-paying W2 position that may be more consistent and make it easier to qualify sooner.

@Eric Gomez NFA's take a long time to arrive, so keep that in mind if you're in a time crunch and need to close sooner than later. 

The sooner you gain these experience, the better investor you will be and that'll take you so much closer to financial freedom. 

Appreciation is an icing on the cake bonus, and depreciation is a temporary setback the market will fix for you sooner or later.

CONSLower revenue potential vs B & BStill need to get the B & B license (and still need to provide "breakfast" even coffee & donuts)STR biz model would mean much hight taxes vs B & B business (from what I understand)HUGE Airbnb competition - area is highly desirable but oversaturatedPROSGreat revenue for an under $500k total investmentQuicker ramp up to produce revenueCan become passive much sooner than a B & B OPTION 3.

In my free-time, you can find me at the gym, going on walks, trying to find the best ice cream in the DC metro area.I've found many entrepreneurs are a bit hard to find as they tend to be solo-preneurs, but I'm very interested in meeting other young professionals with similar goals to bring one another up.

Leaving me more money now to invest sooner.