If your sources of income continue to be an issue, press pause on the property search altogether and look to make a shift into more conventional sources of income (or otherwise regulate your income in some fashion)- What this shift entails is a completely different issue - for example, if lenders would like to see a higher earnings level, this is a different question than seeing steadier/more regular earningsObviously I don't know the full context around your earnings situation, which is why bullet point #2 is extra light and only comes after exhausting other available options within the scope of your current lifestyle.

I am a young eager to learn aspiring real estate investor and want to get involved in some fashion or another immediately.

I suppose that is where this crazy ride started.

You may be just the person he's been waiting for to ride in on a white horse and help him solve this problem he's got on his hands...and solving problems/adding value is how you make money. :)

I am currently located in Weymouth, MA a short ride south of Boston proper. 

Does this seem reasonable or am I being taken for a ride? 

To answer your other question, we would plan to hold and ride the cash flow wave; hopefully up.  

And of course folks bragging about their killer interest rate while listening to "Hipster Cocktail Party" on Pandora might not mention that they spent 2 or 3 discount points buying it down as a fashion choice, not necessarily a rational economic one.You can't day-trade when you go into contract, nor are you in a position to alter the presidential election results, but you can (and should) day-trade when you refinance.

I would also HIGHLY recommend:Jupiter/Juno Beach/Palm Beach GardensDelray BeachParkland/Coral Springs/Sunrise (Parland gets lots of mentions for schools, lack of crime, etc. but it's far from the ocean and you will see lots of gators)HollywoodPompano BeachBoca RatonWellingtonCoconut CreekMiami Beach (fashion)That is a good sampling.  

Having said that, I believe you buy in times of distress and ride the recovery.