I do not recall there being a cost seg portion related to the STRs that make It better but I'm sure doing a standard cost set will also help for tax purposes depending on your goals. 

So, I'd like to correctly categorize things for 2024.Anyway...supplies vs assets. 

Overall Cost-Effectiveness: Is there any real financial benefit to taking this route, or is it essentially the same as just selling?

I should be paying the entire amount back no later than April of 2023 and maybe as soon as January 2023. 

@Leah MillerTypically no - condo bylaws and zoning regulations typically do not allow to segment a units potential exists to possibly combine units (which can be cost prohibitive as you need board approval and potential building code issues) but I have never seen a condo building allow someone to subdivide a unit

The layout of the lot would have to be just right (for example a corner lot) and the main house may need to be discounted depending on what's happening there (for example if now there is no garage, part of the backyard was chopped, etc.). 

Repair & installation costs in the Boston area are some of the highest in the country.- Watch out for residential tax exemptions, and be aware of which towns / cities have them.

No major roads between the house and the beach?

So far so good, still in claim processes but no hiccups just yet...

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