Is there anything you can switch up strategy wise or do you need to expand your search a little outside Boston?

I would go the VA loan if you can, no pmi will help your debt ratio as well.  

So before dismissing your options, you may want to consult an investor friendly Lender who is an out of the box thinker.

I don’t see where a rental would make sense, so I’m trying to look at other options to cover the monthly payments until the market goes back up.  

That likely means that they are not good with money management which you are likely expecting from him.To answer your question, if you are doing long-term rentals, the LLC taxed as a partnership is likely the go to route.Best of luck.  

At the end of the day; you need more money to do something like this.MAX LTV on new builds is 80% LTC, Meaning if the build is $550,000 and Land is XAdd ($550,000 + x ) * .8 = LOAN AMOUNTYou would need to come in with MINIMUM 20% of the cost in addition to closing costs and reserves, $80,000 is not going to cut it for this project.

I live in San Diego and am trying to purchase my first investment property I have about 150K to put down but am struggling to find deals that meet my price point. 

There are a few options.1.

You’d be more likely to get away without parking for tenants but even then, what kind of tenant are you going to attract?

You should create a presentation to demonstrate how you intend to use their money and what they can expect in return.