I'm coming to the realization that it's not feasible for everyone to do both but, when done correctly as in w/ @Russell Brazil's case, it can be extra lucrative.

Any feasible VRs will need to be on the beach or have beach views and be close to destined shopping and entertainment venues equalling a high purchase cost.

Now, if I am wrong and they DO allow the seller to be in second position, is that a feasible option?

Any preferences for cloud based document storage and sharing?

You didn't include your age, but If you were to do this a few times, be patient and buy smart, it's entirely feasible that you could "retire" after a few years.

Let me start this by saying that I am not in the least familiar with REI in NYC!  Been to the city several times, love it, know people who've lived in various types of housing there, but that's it.Someone found my com...

Find out what kind of issues they have with the property (ie: leaks, hot water, termites, rats, noise, crime, what they think about the other tenants, when their last house call/repair was, what parking storage/storage goes with which unit, etc) You can get a lot of insights and points of further investigation this way.   

Simultaneously research rents, and separately sale prices for similar properties.These data points will tell you whether it's feasible to build on the site.

Im holding it for sentimental and storage reasons.

I imagine it would take 10 to 15 years to recoup this investment, which doesn't seem worth it to me.I'm wondering what other options are feasible, such as purchasing existing construction plans, building a pre-fab, or anything else I'm not thinking of, to decrease the cost and time-to-break-even.Thanks!