@Nicholas Hytla as long as you still have some VA benefit left and you met the minimum residency requirement you may use the first property as a rental and use more of your benefit for an additional (new) home.

Brandon Turner and David Greene talked about building additional rooms (assuming the zoning will allow it) on a recent BP podcast.

Rehab: $50,000 (seller's agent information)ARV: $180,000Rent: Both units combined should rent for $1800/month (could potentially be upwards of $2200 with higher quality rehab)Monthly cashflow = $470(see photo of analysis for additional info)meaning...

In addition, my parents and I started a small frozen custard store back in 2016 which I love running (and eating.... maybe to much!?) 

AIM: FLIP to start and build up additional liquidIty with a long term focus on the BRRRR strategy and generating sustainable cashflow through multI-family properties.

To install solar panels and a geothermal heat pump in the Boston area might cost about $100K retail, which seems like a non-starter UNLESS incorporating these into a mortgage made financial sense for the buyer, and...appraisers factored this into the appraisal valueSo in other words, if the additional amount on a 30 year mortgage were offset by energy savings & programs, AND the buyer was able to live carbon-free, it seems that this might attract a savvy and enlightened buyer.

In addition, there was no refrigerator in the kitchen when we received the key.

He stated that he is legally unable to harm either party, but doesn't have that fiduciary responsibility. 

Additionally, I am looking to transition my career into something more RE oriented, as I am currently a project manager in a media company, and have been in Managerial/HR positions for the past 8+ years in non-RE fields.

If you make renovations and/or additions to the property which will increase the value of the property, it is possible to refinance and pull equity out.