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

**The size or nature of the animal makes it impossible to house safely our humanely.

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. 

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

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. 

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. 

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

This means your annual housing costs would be $31,632 /yr.Now, owning a home means you own an asset, so this asset will naturally appreciate.

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..