Estimated costs range from $500–$1,000 annually, depending on the complexity of their LLC and rental activity.For Partner 2 ($148K joint income, W-2, 1099 income, 1 rental, 2 kids), a CPA is strongly recommended.

the value added versus cost to add, especially in single family zoned areas, typically results in a large negative initial position.  

It will likely be cheaper than the cost of financing.

Lets say its $270k and you are financing $220k and it takes a year at 12% thats $26k in interest plus other costs etc.

Oil heating costs are outrageous and you also have to deal with leaking tanks which can be a nightmare.

Also, you can't know how the cost of materials could fluctuate over your project time, so consider purchasing any materials upfront so you can stick to your budget. 

You want a design that stays relevant, withstands high turnover, and doesn’t require constant costly updates.7.

Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

I paid about $1500 in closing costs between title, appraisal, etc, but the original loan was wiped out in favor of a new lower rate. 

VA loans are the only loans that allow this, and there is no rate penalty for it no longer being your primary home.With that in mind, you could do a cash out refinance today at a higher rate than current market rates which will create profit on the loan, we can take that profit to pay for your closing costs.