If you are using your own homeowner's insurance premium as a baseline, then you first need to recognize that a homeowner's insurance policy and a non-owner occupied investment property policy are not the same . 

@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.

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.