These type living arrangements are primarily short term until user circumstances change

I have a rental in Danbury and short term rentals out of state. 

Although the study may increase the gain, the gain may be taxed at a much lower rate making it a beneficial investment.If a property is purchased with the intention to flip or own for a short period of time (less than 3 years), a cost segregation study may not be significant.Overall, as long as you intend to hold the investment property for greater than a year, the benefits of a cost segregation study should be considered.

It will likely be a web of contractors, engineers, and architects, but some those are ultimately leading to the developer. 

Short term rentals are a lot of work. 

A formal business built on this seems overkill as you’re essentially paying someone for a service that already has standard model.If you and the parnter have distinct business tasks/abilities (i.e. not what you would hire an agent or contractor for), such as off-market lead generation, that’s a different discussion.

It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

Whichever method of lead generation you decide on, aim to establish and maintain a relationship with prospective sellers. 

Based on your current assumptions, you would be paying $1,229 per month out of pocket, leading to negative cash flow.If you’re house hacking and living in the property, it might still make sense because you're paying for housing anyway.

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