I also saw your profile and I need a roofing contractor so please pm me for future projects.

I'm sure I'll be contacting you in the near future!

However, this home is in Berkeley and I am concerned about destroying historical elements and potential added structural engineering costs that could make the house attractive to a buyer in future years, along with the opportunity cost of construction now versus getting rental income from the house in the next few months. 

With $200 a month in rent (just used a high number to account for future increases in rent) if you rented it out, it'd take about 10-12 years or so to match that 30k.3) Have a meeting with your realtor and discuss your displeasure with his strategy.

I honestly don’t recommend this for you just cause you don’t seem experienced enough to successfully pull this off and the downfall is wasting an investors time, whatever appraisal will cost you, and losing an investor with tons of possible future deals because you bit more than you can chew on your first deal with him.

You are smart to start at 25 and build your future early. 

That might be an option for the future, but I don't think I am experienced enough to go that route yet. 

I think there's a strong future for STR in Colorado Springs and like @Jenn N.

She likes what I have shown her... the numbers... the potential future. 

You can file it at any point in the year and the adjustment will go against future taxes, sometimes eliminating the next few quarterly payments or more.