Will be helpful to rerun the models based off your guidance.

I'm no stranger to home renovations, I've had experience resurfacing hardwood, putting up drywall, installing dryers, etc on my dad's property.

Based from your experience, is it better to keep the pool or retire it?

Some may be great options for base annual cashflow. 

Make sure you use net cash flow, so you are accounting for maintenance, repairs, cap ex, vacancy, and property management; based on the numbers you provided your net cash flow is probably less than $1k per year. 

Is it usually a 6 month seasoning before being able to go for new appraisal and getting financed based on the ARV rather than cost.I've done a lot of reading and from what I understand this is possible, just looking for verification, recommendations on path forward or alternate plan, and also some lender referrals for when this takes place. 

Commercial real estate are not based on comps, but on Net Operating Income and Caprate.

If you are looking for true private money (no broker fee or points) most will not lend at a high leverage. 60-65 LTV max Now if you have experience, plenty of reserves, and the deal can be 100% financed based on the ARV, then you can present it to a hard money lender and they may feel comfortable doing it. 

Right now we have 2 units that are vacant, ready, and being marketed, and with the 'asking rent' reductions we just did to try to fill them faster (it's offseason for leasing), the estimated market value of the building based on net operating income is now $1,542,500.

Based upon your post the Greater Boston area and markets even slightly outside definitely seem to fit what you are looking for so just wanted to see if there was something you were considering as a negative factor..